JP5554082B2 - Pigment dispersion composition, colored curable composition, color filter, liquid crystal display device, and solid-state imaging device - Google Patents

Description

  The present invention relates to a pigment dispersion composition having excellent pigment dispersibility, a colored curable composition using the same, a color filter produced using the colored curable composition, and a liquid crystal display device including the color filter And a solid-state imaging device.

  In recent years, color filters tend to be used not only for monitors but also for televisions (TVs) in liquid crystal display (LCD) applications. With this trend of application expansion, advanced color characteristics in chromaticity, contrast, etc. Has come to be required. Similarly, in image sensor (solid-state imaging device) applications, advanced color characteristics such as reduction in color unevenness and improvement in color resolution are required.

  In response to the above requirements, it is required to disperse the pigment in a finer state (good dispersibility) and to disperse in a stable state (good dispersion stability). If the dispersibility of the pigment is insufficient, fringes (jagged edges) and surface irregularities occur in the formed colored resist film, resulting in a decrease in chromaticity and dimensional accuracy of the produced color filter, and contrast. There is a problem that it is significantly deteriorated.

  In addition, when the dispersion stability of the pigment is insufficient, in the color filter manufacturing process, in particular, the uniformity of the film thickness in the coating process of the colored curable composition is reduced, or the exposure in the exposure process. There is a tendency that the sensitivity is lowered and the alkali solubility in the developing process is lowered. Furthermore, when the dispersion stability of the pigment is poor, the components of the pigment dispersion composition and the colored curable composition are agglomerated with the passage of time, the viscosity increases, and the pot life is extremely shortened. There is also a problem.

In order to solve such a problem, a polymer-type pigment dispersant in which an organic dye structure and a polymer are combined has been proposed (see Patent Document 1).
However, since the surface area of the pigment particles is increased when the pigment particle size is reduced, the cohesive force between the pigment particles is increased, and it is difficult to achieve both a high level of dispersibility and dispersion stability.

  In producing a color filter using a colored curable composition containing a pigment dispersion composition, the colored curable composition is applied and dried on a substrate or a substrate on which a light-shielding layer having a desired pattern has been previously formed. After that, the dried coating film is irradiated with radiation in a desired pattern (hereinafter referred to as “exposure”) and developed to obtain pixels of each color.

  However, the color filter manufactured in this manner is likely to cause residue and background contamination on the unexposed substrate or the light shielding layer in the development process, and the post-baked pixels after development have poor surface smoothness. There was a problem that the physical properties of the coating film were inferior. Moreover, the degree of deterioration of residues, background stains and surface smoothness on the substrate or the light-shielding layer tends to become more prominent as the concentration of the pigment contained in the colored curable composition increases. With a colored curable composition, it has been difficult to achieve a sufficient color density.

  Further, for the purpose of imparting alkali developability, a pigment dispersion composition using a block type, random type, or linear polymer compound into which acrylic acid is introduced as an alkali-soluble resin is known (Patent Documents 2 and 3). The pigment dispersibility and developability when applied to a curable composition for pattern formation such as a color filter are still insufficient.

  In addition, when such a pigment dispersant is applied to a curable material, a method of introducing a polymerizable group into a polymer compound has been proposed for the purpose of improving the curability. Acrylate resins (for example, see Patent Document 4) and alkali-soluble acrylic resins (for example, see Patent Document 5) are known. However, although these polymer compounds are improved in curability, the dispersibility of fine pigments is not sufficient.

  In recent years, color filters are required to have a higher color density as the thickness of the color filter is increased. In order to form a color filter with a high color density, it is necessary to increase the color material density in the colored resin composition to be used, but the components that contribute to image forming properties such as solubility in an alkaline developer are relatively As a result, the image forming performance originally possessed by the resin composition deteriorates. In order to solve these problems, attempts have been made to maintain the image forming property while maintaining the colorant concentration high by using a dispersant having both a dispersing function and a binder function. A pigment dispersion composition using a linear polymer compound such as a block type or a random type into which an acid is introduced is also known (see Patent Document 3). However, in particular, an extremely fine pigment has a sufficient dispersibility. Not in.

JP 2008-009426 A Japanese Patent No. 3094403 JP 2004-287409 A JP 2000-321863 A JP 2003-029018 A

The object of the present invention made in consideration of the above problems is a pigment dispersion excellent in dispersion stability, and the curability by applying energy and the developability of the uncured portion using the pigment dispersion are good. The object is to provide a colored curable composition having excellent formability.
Another object of the present invention is to provide a high-quality color filter having a colored pattern using the colored curable composition, and further, the color filter provided with the color filter is excellent in color reproducibility, An object of the present invention is to provide a high-contrast liquid crystal display device and a high-resolution solid-state imaging device with small color unevenness.

As a result of intensive studies, the present inventor has found that the above problem can be solved by using a polymer compound having a specific main chain structure and pendant with a polymerizable group in the side chain, leading to the present invention. It was.
That is, the object of the present invention is achieved by the following means.

<1> (A) An unsaturated double bond is pendant on a side chain of a polymer containing 5% by mass to 30% by mass of at least one of acrylic acid and methacrylic acid as a main chain skeleton, and Contains a graft type polymer having at least one repeating unit selected from repeating units represented by the following general formula (1) and general formula (2), (B) a pigment, and (C) an organic solvent Pigment dispersion composition.

[In General Formulas (1) and (2), R ¹ , R ² , R ⁴ , and R ⁵ each represent a hydrogen atom, and R ³ and R ⁶ each independently represent a hydrogen atom or a methyl group . X ¹ and ^{X 2} are each independently, - C (= O) O - represents a. L ¹ and L ² each independently represent an ethylene group or —C ₂ H ₄ —NHC (═O) — . A ¹ and A ² each independently represents a linear substituted or unsubstituted alkyl group having 4 to 15 carbon atoms or a branched substituted or unsubstituted alkyl group having 4 to 15 carbon atoms. Represent. m and n represent 5 . p and q are each independently an integer of 4-10. ]
<2> An unsaturated double bond is pendant on the side chain of the polymer containing 5% by mass to 30% by mass of at least one of acrylic acid and methacrylic acid as a copolymer component in the main chain skeleton (A), And the graft type polymer having at least one repeating unit selected from the repeating units represented by the general formula (1) and the general formula (2) further contains a heterocyclic structure in the side chain, And the pigment dispersion composition as described in <1> whose weight average molecular weights are 1,000-100,000.
<3> When the total amount of acrylic acid and methacrylic acid contained in the graft polymer as a copolymerization component is 100, the ratio (mass ratio) of acrylic acid is 80 or more <1> or <2> The pigment dispersion composition described in 1.
<4> The pigment dispersion composition according to any one of <1> to <3>, wherein an average primary particle diameter of the (B) pigment is in a range of 10 nm to 25 nm.
<5> The pigment dispersion composition according to any one of <1> to <4>, which is used for forming a colored region in a color filter.

< 6 > A colored curable composition containing the pigment dispersion composition according to any one of <1> to < 5 >, a polymerizable compound, and a photopolymerization initiator.
< 7 > The colored curable composition according to < 6 >, wherein the concentration of the pigment (B) is 35% by mass or more and 90% by mass or less.
< 8 > A color filter comprising the colored curable composition according to < 6 > or < 7 >.
< 9 > A liquid crystal display device using the color filter according to < 8 >.
< 10 > A solid-state imaging device using the color filter according to < 8 >.

The operation of the present invention is not clear, but is considered as follows.
In the pigment dispersion composition of the present invention, (A) an unsaturated double bond is present in the side chain of a polymer containing at least one of acrylic acid and methacrylic acid in the main chain skeleton as a copolymerization component in an amount of 5 to 30% by mass. A pendant graft polymer is used as a pigment dispersant. The high molecular polymer used here has (meth) acrylic acid in the main chain and is a graft type, so that the main chain (meth) acrylic acid has a relatively high polarity and the main chain is flexible. Therefore, even when a highly polar pigment is used as the pigment, the main chain (meth) acrylic acid effectively coats the pigment and the graft chain functions as a steric repulsion chain. It is thought that re-aggregation of the material was suppressed. Therefore, by using the graft type polymer according to the present invention as a pigment dispersant, the secondary aggregate that is an aggregate of primary particles of the pigment is effectively loosened, and the primary particles are It is considered that reaggregation into secondary aggregates can be effectively suppressed. Therefore, it is considered that in the dispersion step, it is possible to obtain a dispersion in a state close to that in which the primary particles of the pigment are dispersed.
In addition, since the graft type polymer according to the present invention has an unsaturated double bond pendant on the side chain, the colored curable composition containing such a pigment dispersion composition is subjected to energy application. Curing is performed with high sensitivity, and even in the deep part of the film formed of the colored curable composition such as the vicinity of the substrate interface, the curing becomes good, the support adherence is excellent, and the pattern shape can be prevented from becoming a reverse taper type. In the exposed area, the graft-type polymer contains the pigment, and the unsaturated double bond is cured by a crosslinking reaction, so the pigment is fixed in the cured film, and the developer or coating liquid Diffusion is suppressed. On the other hand, in the unexposed area, pigment aggregation is suppressed by the graft type polymer, so that the developer permeates quickly, and good developability of the unexposed area is maintained.
Accordingly, since the colored pattern formed by such a colored curable composition has a good pattern shape while the pigment is uniformly dispersed therein, the color filter provided with this has high contrast, It is considered to be a high-quality color filter with small color density unevenness.

According to the present invention, a pigment dispersion having excellent dispersion stability, and a colored curable composition using the pigment dispersion, having excellent curability by applying energy and developability of an uncured portion, and having excellent pattern formability. Can be provided.
In addition, according to the present invention, a high-quality color filter having a color pattern using the colored curable composition of the present invention, and further comprising the color filter, having excellent color reproducibility and high contrast. A liquid crystal display device and a high-resolution solid-state imaging device with small color unevenness can be provided.

The present invention will be described in detail below.
The present invention, in a side chain of a polymer comprising at least one as a 5% to 30% by weight copolymer component of acrylic acid and methacrylic acid (A) a main chain skeleton, unsaturated double bonds are pendent and later to the general formula (1) and the general formula (2) that have a least one repeating unit selected from repeating units represented by the graft polymer copolymer (hereinafter, referred to as the specific graft polymer A pigment dispersion composition comprising (B) a pigment, and (C) an organic solvent, and (A) a graft polymer compound copolymerized with acrylic acid on the main chain if necessary. A polymer compound containing a heterocyclic ring in the side chain.

<(A) Specific graft polymer>
First, the main chain structure of the specific graft polymer used in the present invention will be described.
If the specific graft polymer of this invention has 1 or more types selected from acrylic acid and methacrylic acid as the principal chain structure, and the content of acrylic acid and methacrylic acid is 5-30 mass% in total, There is no particular restriction. In addition, the weight average molecular weight of the graft polymer is preferably in the range of 1,000 to 100,000.
Hereinafter, in the present specification, when referring to either or both of acrylic acid and methacrylic acid, it may be expressed as (meth) acrylic acid.

About the specific graft polymer, the (meth) acrylic acid group should just be included in the principal chain, and the (meth) acrylic acid group may be further included in the branch part.
Synthetic methods for forming the main chain structure of a specific graft polymer are as follows: (1) Branched monomer from main chain polymer as described in New Polymer Experiments Vol. 2 (Kyoritsu Shuppan, 1995). (2) A method of bonding a branched polymer to a main chain polymer, (3) A method of copolymerizing a main chain monomer with a branched polymer, and the like can be used. In this synthesis, an unsaturated double bond may be introduced by a polymer reaction or the like. Further, as described later, an unsaturated double bond can be introduced by copolymerizing a structural unit having an unsaturated double bond having a protecting group in the side chain and then removing the protecting group.
Moreover, you may introduce | transduce an unsaturated double bond with respect to the polymer synthesize | combined using it as a copolymerization component.
That is, the main chain structure of the specific graft polymer that can be used in the present invention is obtained by copolymerizing (meth) acrylic acid, a polymerizable oligomer (hereinafter referred to as a macromonomer) and another copolymerizable monomer. It is.

The introduction amount of (meth) acrylic acid is required to be 5 to 30% by mass from the viewpoint of dispersibility. If it exceeds 30% by mass, the amount of macromonomer to be copolymerized becomes relatively small, so that the steric repulsion chain does not contribute and sufficient dispersion stability cannot be obtained. On the other hand, if it is 5% by mass or less, sufficient flexibility cannot be obtained as a whole polymer compound, and it is difficult to obtain the effects of improving dispersion stability and developability. Furthermore, although the amount of acrylic acid introduced depends on the type and molecular weight of the macromonomer, it is preferably 10 to 30% by mass, and most preferably 10 to 25% by mass.
Here, the ratio of acrylic acid and methacrylic acid is arbitrary, but from the viewpoint of interaction formation with the pigment, it is preferable that there is more acrylic acid, and the preferred ratio (mass ratio) is that of acrylic acid and methacrylic acid. When the total amount is 100, acrylic acid is preferably 80 or more.
A preferable structure derived from a macromonomer useful for forming such a main chain structure is a repeating unit represented by the following general formula (1) and general formula (2), or a macro represented by general formula (3). It has a repeating unit derived from a monomer. The specific graft polymer has at least one repeating unit selected from repeating units represented by the following general formula (1) and general formula (2). Most preferably, the repeating unit is In the specific graft polymer in the present invention, among the repeating units represented by the general formula (1) and the general formula (2) described in detail below, R ¹ , R ² , R ⁴ , and R ⁵ are hydrogen atoms. the stands, ^{R 3} and ^{R 6} each independently represents a hydrogen atom or a methyl group, ^{X 1} and ^{X 2} are, each independently, -C (= O) O- the stands, is ^{L 1} and ^{L 2} Each independently represents an ethylene group or —C ₂ H ₄ —NHC (═O) —, wherein A ¹ and A ² are each independently a linear substituted or non-substituted group having 4 to 15 carbon atoms. Represents a substituted alkyl group or a branched substituted or unsubstituted alkyl group having 4 to 15 carbon atoms, m and n represent 5, p and q each independently represents an integer of 4 to 10 Having at least one repeating unit selected from the repeating units represented The

In general formulas (1) and (2), R ^{1 to} R ⁶ each independently represents a hydrogen atom or a monovalent organic group. X ¹ and X ² each independently represent —CO—, —C (═O) O—, —CONH—, —OC (═O) —, or a phenylene group.
L ¹ and L ² each independently represents a single bond or an organic linking group.
A ¹ and A ² each independently represents a monovalent organic group.
m and n each independently represents an integer of 2 to 8.
p and q each independently represents an integer of 1 to 100.

R ^{1 to} R ^{6 each} represents a hydrogen atom or a monovalent organic group. As the monovalent organic group, a substituted or unsubstituted alkyl group is preferable. As an alkyl group, a C1-C12 alkyl group is preferable, a C1-C8 alkyl group is more preferable, and a C1-C4 alkyl group is especially preferable.
When the alkyl group has a substituent, examples of the substituent include a hydroxy group, an alkoxy group (preferably having 1 to 5 carbon atoms, more preferably 1 to 3 carbon atoms), a methoxy group, an ethoxy group, Examples include a cyclohexyloxy group.

Specific examples of preferred alkyl groups include methyl, ethyl, propyl, n-butyl, i-butyl, t-butyl, n-hexyl, cyclohexyl, 2-hydroxyethyl, 3 -A hydroxypropyl group, 2-hydroxypropyl group, 2-methoxyethyl group is mentioned.
R ¹ , R ² , R ⁴ and R ⁵ are preferably hydrogen atoms, and R ³ and R ⁶ are most preferably hydrogen atoms or methyl groups from the viewpoint of adsorption efficiency on the pigment surface.

X ¹ and X ² represent —CO—, —C (═O) O—, —CONH—, —OC (═O) —, or a phenylene group. Among them, —C (═O) O—, —CONH—, and a phenylene group are preferable from the viewpoint of adsorptivity to the pigment, and —C (═O) O— is most preferable.

L ¹ and L ² represent a single bond or an organic linking group. As the linking group, a substituted or unsubstituted alkylene group is preferable. The alkylene group is preferably an alkylene group having 1 to 12 carbon atoms, more preferably an alkylene group having 1 to 8 carbon atoms, and particularly preferably an alkylene group having 1 to 4 carbon atoms.
More preferably, the alkylene group is linked via a hetero atom (for example, an oxygen atom, a nitrogen atom, or a sulfur atom).
Specific examples of preferable alkylene groups include a methylene group, an ethylene group, a propylene group, a trimethylene group, and a tetramethylene group. When the alkylene group has a substituent, examples of the substituent include a hydroxy group.
The organic linking group is a heteroatom selected from —C (═O) —, —OC (═O) —, —NHC (═O) —, or a partial structure containing a heteroatom, at the terminal of the above alkylene group. And those linked via a heteroatom or a partial structure containing a heteroatom are preferred from the standpoint of adsorptivity to the pigment.

A ¹ and A ² represent a monovalent organic group. The monovalent organic group is preferably a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
Examples of preferable alkyl groups include linear, branched, and cyclic alkyl groups having 1 to 20 carbon atoms. Specific examples thereof include a methyl group, an ethyl group, a propyl group, Butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, hexadecyl, octadecyl, eicosyl, isopropyl, isobutyl, s-butyl, Examples thereof include t-butyl group, isopentyl group, neopentyl group, 1-methylbutyl group, isohexyl group, 2-ethylhexyl group, 2-methylhexyl group, cyclohexyl group, cyclopentyl group and 2-norbornyl group.

As A ¹ and A ² , from the viewpoint of dispersion stability and developability, a straight chain having 1 to 20 carbon atoms, a branched structure having 3 to 20 carbon atoms, and a number having 5 to 20 carbon atoms Cyclic alkyl groups are preferable, linear alkyl groups having 4 to 15 carbon atoms, branched alkyl groups having 4 to 15 carbon atoms, and cyclic alkyl groups having 6 to 10 carbon atoms are more preferable. A straight chain of 6 to 10 and a branched chain of 6 to 12 carbon atoms are more preferable.

m and n each independently represents an integer of 2 to 8. In view of dispersion stability and developability, 4 to 6 is preferable, and 5 is most preferable.
p and q each independently represent an integer of 1 to 100. Two or more different p and different q may be mixed. p and q are preferably 5 to 60, more preferably 5 to 40, and still more preferably 5 to 20 from the viewpoints of dispersion stability and developability.
From the viewpoint of dispersion stability, the repeating unit represented by the formula (1) is preferable.
Moreover, the repeating unit represented by Formula (1-2) is more preferable.

L ^a represents an alkylene group having 2 to 10 carbon atoms, and L ^b represents —C (═O) — or —NHC (═O) —. R ^{1 to} R ³ , m, p, and A ¹ have the same meaning as in formula (1).

  The repeating units represented by the formulas (1), (2), and (1-2) are polymers or copolymers of monomers represented by the following formulas (i), (ii), and (i-2), respectively. By polymerization, it is introduced as a repeating unit of the polymer compound.

In the formula (i), formula (ii), and formula (i-2), R ^{1 to} R ⁶ , X ¹ , X ² , L ¹ , L ² , m, n, p, q, A ¹ , A ² , L ^a , and L ^b are synonymous with those in Formula (1), Formula (2), and (1-2). These synthesis methods can be obtained, for example, by adding a monocarboxylic acid or monoalcohol to ε-caprolactone to initiate ring-opening polymerization.
Preferred specific examples of the monomers represented by formulas (i), (ii) and (i-2) [monomer (A-1) to monomer (A-15)] are listed below. The present invention is not limited to these.

In the general formula (3), R ⁷ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and W is a single bond or alkylene, alkenylene, cycloalkylene, phenylene, ether, thioether, ester, carbonyl, amino , An amide, a sulfonylamide, a single linking group selected from an atomic group represented by urethane, or a linking group formed by arbitrarily combining two or more thereof. A ³ represents a partial structure containing a repeating unit derived from a radical polymerizable monomer such as (meth) acrylic acid ester, (meth) acrylonitrile, styrene derivative, (meth) acrylamides and the like.

  Specific examples of the macromonomer represented by the general formula (3) include the following.

In the above, A has the same meaning as A ³ in formula (3), and the partial structure represented by A includes polymethyl methacrylate, polybutyl methacrylate, polystyrene, methyl methacrylate-butyl methacrylate copolymer, methyl methacrylate-styrene. And a copolymer.

The weight average molecular weight of the specific graft polymer is preferably 1,000 to 100,000, more preferably 3,000 to 100,000, and 5,000 to 50,000. Is more preferable, and the range of 10,000 to 30,000 is most preferable. When the weight average molecular weight is 1,000 or more, a stabilizing effect can be obtained more effectively, and when the weight average molecular weight is 100,000 or less, it is more effectively adsorbed and has good dispersibility. Can be demonstrated.
In particular, the weight average molecular weight of the branch part (side chain) is preferably 300 to 10,000. More preferably, it is 500-5,000, More preferably, it is 1,000-3,000. When the molecular weight of the branch is in the above range, the developability is particularly good and the development latitude is wide.

  The specific graft polymer may contain only one type of repeating unit composed of a macromonomer, or may contain two or more types. In the specific graft polymer, the content of the repeating unit composed of the macromonomer is not particularly limited, but when the total structural unit contained in the specific graft polymer is 100% by mass, the content is 5% by mass or more. Is preferable, it is more preferable to contain 40-90 mass%, and it is further more preferable to contain 50-80 mass%.

Other monomers that can be combined to form the main chain of the specific graft polymer include (1) a monomer having an organic dye structure or a heterocyclic structure, (2) a monomer having an acidic group, (3) basic A monomer having a nitrogen atom, (4) a monomer having a urea group, a urethane group, a coordinating oxygen atom, a hydrocarbon group having 4 or more carbon atoms, an alkoxysilyl group, an epoxy group, an isocyanate group, or a hydroxyl group, (5) Monomers containing ionic functional groups, (6) (meth) acrylic acid esters, crotonic acid esters, vinyl esters, maleic acid diesters, fumaric acid diesters, itaconic acid diesters, (meth) acrylamides, Styrene, vinyl ethers, vinyl ketones, olefins, maleimides, (meth) acrylonitrile, and other modules Optionally you can select one or more mer. Among these, it is particularly preferable to have (1) from the viewpoint of adsorption power to the pigment.
The copolymerizable monomer used when introducing the unsaturated double bond into the specific graft polymer according to the present invention will be described in detail separately.

  The monomer (1) having an organic dye structure or a heterocyclic structure is preferably a monomer represented by the following general formula (4), a maleimide, or a maleimide derivative. A monomer represented by the following general formula (4) is particularly preferable.

In general formula (4), R ⁸ represents a hydrogen atom or a substituted or unsubstituted alkyl group. R ⁹ represents a single bond or a divalent linking group. P represents -CO-, -C (= O) O-, -CONH-, -OC (= O)-, or a phenylene group. Q represents a group having a nitrogen-containing heterocyclic structure.

In General Formula (4), R ⁸ represents a hydrogen atom or a substituted or unsubstituted alkyl group, and the alkyl group is preferably an alkyl group having 1 to 12 carbon atoms, and an alkyl group having 1 to 8 carbon atoms. Group is more preferable, and an alkyl group having 1 to 4 carbon atoms is particularly preferable.
When the alkyl group represented by R ⁸ has a substituent, examples of the substituent include a hydroxy group and an alkoxy group (preferably having 1 to 5 carbon atoms, more preferably 1 to 3 carbon atoms). A methoxy group, an ethoxy group, a cyclohexyloxy group, etc. are mentioned.
Specifically, preferred examples of the alkyl group represented by R ⁸ include, for example, methyl group, ethyl group, propyl group, n-butyl group, i-butyl group, t-butyl group, n-hexyl group, cyclohexyl group, 2 -Hydroxyethyl group, 3-hydroxypropyl group, 2-hydroxypropyl group, 2-methoxyethyl group can be mentioned.
R ⁸ is most preferably a hydrogen atom or a methyl group.

In General Formula (4), R ⁹ represents a single bond or a divalent linking group. The divalent linking group is preferably a substituted or unsubstituted alkylene group. As this alkylene group, a C1-C12 alkylene group is more preferable, a C1-C8 alkylene group is more preferable, and a C1-C4 alkylene group is especially preferable.

The alkylene group represented by R ⁹ may be one in which two or more are connected via a hetero atom (for example, an oxygen atom, a nitrogen atom, or a sulfur atom).
Specific examples of the preferable alkylene group represented by R ⁹ include a methylene group, an ethylene group, a propylene group, a trimethylene group, and a tetramethylene group.
When the preferable alkylene group represented by R ⁹ has a substituent, examples of the substituent include a hydroxy group.
Examples of the divalent linking group represented by R ⁹ include —O—, —S—, —C (═O) O—, —CONH—, —C (═O) S at the end of the alkylene group. A heteroatom or a heteroatom selected from-, -NHCONH-, -NHC (= O) O-, -NHC (= O) S-, -OC (= O)-, -OCONH-, and -NHCO- It may have a partial structure and may be linked to Q via the heteroatom or a partial structure containing a heteroatom.

  In general formula (4), Q represents a group having a heterocyclic structure. Examples of the group having a heterocyclic structure include phthalocyanine, insoluble azo, azo lake, anthraquinone, quinacridone, dioxazine, diketopyrrolopyrrole, anthrapyridine, ansanthrone, indanthrone, and flavan. Throne, perinone, perylene, thioindigo dye structures, such as thiophene, furan, xanthene, pyrrole, pyrroline, pyrrolidine, dioxolane, pyrazole, pyrazoline, pyrazolidine, imidazole, oxazole, thiazole, oxadiazole, triazole, Thiadiazole, pyran, pyridine, piperidine, dioxane, morpholine, pyridazine, pyrimidine, piperazine, triazine, trithiane, isoindoline, isoindolinone, benzimidazolone, Heterocycles such as zothiazole, succinimide, phthalimide, naphthalimide, hydantoin, indole, quinoline, carbazole, acridine, acridone, anthraquinone, pyrazine, tetrazole, phenothiazine, phenoxazine, benzimidazole, benztriazole, cyclic amide, cyclic urea, cyclic imide Structure is mentioned. These heterocyclic structures may have a substituent, and examples of the substituent include an alkyl group, an alkoxy group, a halogen atom, an aliphatic ester group, an aromatic ester group, an alkoxycarbonyl group, and the like. Can be mentioned.

  Q is more preferably a group having a nitrogen-containing heterocyclic structure having 6 or more carbon atoms, and particularly preferably a group having a nitrogen-containing heterocyclic structure having 6 to 12 carbon atoms. Specific examples of the nitrogen-containing heterocyclic structure having 6 or more carbon atoms include phenothiazine ring, phenoxazine ring, acridone ring, anthraquinone ring, benzimidazole structure, benztriazole structure, benzthiazole structure, cyclic amide structure, and cyclic urea structure. And a cyclic imide structure are preferable, and a structure represented by the following general formula (5), (6) or (7) is particularly preferable.

In the general formula (5), X is a single bond, an alkylene group (for example, a methylene group, an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, etc.), -O-, -S-, -NR ^A- , and It is one selected from the group consisting of —C (═O) —. Here, R ^A represents a hydrogen atom or an alkyl group. When R ^A represents an alkyl group, the alkyl group is preferably an alkyl group having 1 to 18 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, such as a methyl group, an ethyl group, or an n-propyl group. I-propyl group, n-butyl group, t-butyl group, n-hexyl group, n-octyl group, 2-ethylhexyl group, n-octadecyl group and the like.
Among the above, as X in the general formula (5), a single bond, a methylene group, —O—, or —C (═O) — is preferable, and —C (═O) — is particularly preferable.

In General Formula (7), Y and Z each independently represent —N═, —NH—, —N (R ^B ) —, —S—, or —O—. R ^B represents an alkyl group, and when R ^B represents an alkyl group, the alkyl group is preferably an alkyl group having 1 to 18 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, for example, a methyl group , Ethyl group, n-propyl group, i-propyl group, n-butyl group, t-butyl group, n-hexyl group, n-octyl group, 2-ethylhexyl group, n-octadecyl group and the like.
Among the above, as Y and Z in the general formula (7), —N═, —NH—, and —N (R ^B ) — are particularly preferable. Examples of the combination of Y and Z include a combination in which one of Y and Z is —N═ and the other is —NH—, and an imidazolyl group.

In general formula (5), (6), or (7), ring B ¹ , ring B ² , ring C, and ring D each independently represent an aromatic ring. Examples of the aromatic ring include a benzene ring, naphthalene ring, indene ring, azulene ring, fluorene ring, anthracene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyrrole ring, imidazole ring, indole ring, quinoline ring, acridine ring, Examples include phenothiazine ring, phenoxazine ring, acridone ring, anthraquinone ring, etc., among which benzene ring, naphthalene ring, anthracene ring, pyridine ring, acridine ring, phenothiazine ring, phenoxazine ring, acridone ring, anthraquinone ring are preferable, benzene A ring, a naphthalene ring, and a pyridine ring are particularly preferable.

Specifically, examples of the ring B ¹ and the ring B ² in the general formula (5) include a benzene ring, a naphthalene ring, a pyridine ring, and a pyrazine ring. Examples of the ring C in the general formula (6) include a benzene ring, a naphthalene ring, a pyridine ring, a pyrazine ring, and the like. Examples of the ring D in the general formula (7) include a benzene ring, a naphthalene ring, a pyridine ring, and a pyrazine ring.
Among the structures represented by ring B ¹ , ring B ² , ring C, and ring D in general formula (5), (6) or (7), from the viewpoint of dispersibility and stability over time of the dispersion, A benzene ring and a naphthalene ring are more preferable. Ring B ¹ , ring B ² and ring D in formula (5) or (7) are more preferably a benzene ring, and ring C in formula (6) is a naphthalene ring. Is more preferable.

  In the specific graft polymer of the present invention, preferred specific examples of the monomer represented by the above general formula (4), maleimide, and maleimide derivatives [Exemplary monomer (M-1) to Illustrative monomer (M-33) )] Are listed below, but the present invention is not limited thereto.

The specific graft polymer may contain only one type of copolymer unit derived from the monomer represented by the general formula (4), maleimide, or maleimide derivative, or may contain two or more types. .
In the specific graft polymer, the content of the copolymer unit derived from the monomer represented by the general formula (4), maleimide, and maleimide derivative is not particularly limited, but the total structural unit contained in the polymer is not limited. When the content is 100% by mass, it is preferable that the copolymer unit derived from the monomer represented by the general formula (4), the maleimide, and the maleimide derivative is contained in an amount of 5% by mass or more, and contained in an amount of 10% by mass to 50% by mass. More preferably.

Among the monomers represented by the general formula (4), maleimide, and maleimide derivatives, the monomer represented by the general formula (4) is preferable because of its high adsorptivity to the pigment.
That is, in order to effectively suppress the formation of secondary aggregates, which are aggregates of primary particles of the pigment, or to effectively weaken the cohesive force of the secondary aggregates, it is represented by the general formula (4). The content of the copolymer unit derived from the monomer, maleimide, and maleimide derivative is preferably 5% by mass or more. From the viewpoint of developability when producing a color filter from a colored curable composition containing a pigment dispersion composition, the content of copolymer units derived from the monomer represented by the general formula (4) Is preferably 30% by mass or less.

  The main main chain structure in the specific graft polymer uses, for example, a monomer represented by the general formula (i), a polymerizable oligomer (macromonomer), and another radical polymerizable compound as a copolymerization component, It can be produced by a normal radical polymerization method. In general, a suspension polymerization method or a solution polymerization method is used. Examples of the solvent used for synthesizing such a specific polymer include ethylene dichloride, cyclohexanone, methyl ethyl ketone, acetone, methanol, ethanol, propanol, butanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, 2-methoxy. Examples include ethyl acetate, 1-methoxy-2-propanol, 1-methoxy-2-propyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, toluene, ethyl acetate, methyl lactate, and ethyl lactate. It is done. These solvents may be used alone or in combination of two or more.

  In the radical polymerization, a radical polymerization initiator can be used, and a chain transfer agent (eg, 2-mercaptoethanol and dodecyl mercaptan) can be further used.

  As a method for introducing an ethylenically unsaturated double bond into a specific graft polymer having such a main chain structure, as a structural unit in which an ethylenically unsaturated double bond is pendant, the following general formula (6) to The aspect which introduce | transduces at least 1 sort (s) as a copolymerization component among the structural units represented by (8) is mentioned preferably.

In the general formulas (6) to (8), A ¹ , A ² , and A ³ are each independently —CO—, —C (═O) O—, —CONH—, —OC (═O). -Represents a phenylene group. G ¹ , G ² , and G ³ each independently represent a divalent organic group. X ³ and Z ¹ each independently represent an oxygen atom, a sulfur atom, or —N (R ⁵² ) —, and R ⁵² represents an alkyl group that may have a substituent. Y ¹ represents an oxygen atom, a sulfur atom, an optionally substituted phenylene group, or —N (R ⁵³ ) —, and R ⁵³ represents an ^optionally substituted alkyl group. m ¹ , m ² , m ³ , n ¹ , n ² and n ³ each independently represents 0 or 1. R ^{31 to} R ⁵⁰ each independently represent a hydrogen atom or a monovalent substituent.

In the general formula (6), R ^{31 to} R ³³ each independently represent a hydrogen atom or a monovalent substituent, preferably a hydrogen atom or an alkyl group which may further have a substituent, and among them, R ³¹ , R ³² is particularly preferably a hydrogen atom, and R ³³ is particularly preferably a hydrogen atom or a methyl group.

R ^{34 to} R ³⁶ each independently represents a hydrogen atom or a monovalent substituent, and R ³⁴ is preferably a hydrogen atom or an alkyl group which may further have a substituent, and among them, a hydrogen atom, a methyl group An ethyl group is particularly preferred. R ³⁵ and R ³⁶ each independently further have a hydrogen atom, a halogen atom, an alkoxycarbonyl group, a sulfo group, a nitro group, a cyano group, an alkyl group that may further have a substituent, or a substituent. An aryl group which may further have a substituent, an aryloxy group which may further have a substituent, an alkylsulfonyl group which may further have a substituent, and further having a substituent An arylsulfonyl group which may be substituted may be mentioned. Among them, a hydrogen atom, an alkoxycarbonyl group, an alkyl group which may further have a substituent, and an aryl group which may further have a substituent are preferable.
Here, examples of the substituent that can be introduced include a methoxycarbonyl group, an ethoxycarbonyl group, an isopropyloxycarbonyl group, a methyl group, an ethyl group, and a phenyl group.

A ¹ in the general formula (6) represents —CO—, —C (═O) O—, —CONH—, —OC (═O) —, or a phenylene group, and in particular, —C (═O) O—. , -CONH-, and a phenylene group are preferable. X ³ represents an oxygen atom, a sulfur atom, or —N (R ⁵² ) —. Here, examples of R ⁵² include an alkyl group which may have a substituent.

G ¹ represents a divalent organic group, and includes an oxygen atom, a nitrogen atom, a sulfur atom, a hydrocarbon ring structure having 3 to 20 carbon atoms, an ester bond, a sulfonate ester bond, and a phosphate ester bond. , A urethane bond, a thiourethane bond, an amide bond, a urea bond, and a thiourea bond, which may have any partial structure, which may have a substituent, The alkylene group of 60 is preferable in terms of performance such as strength and developability. G ¹ is composed of an oxygen atom, a nitrogen atom, a sulfur atom, a hydrocarbon ring structure having 3 to 20 carbon atoms, an ester bond, a urethane bond, a thiourethane bond, an amide bond, a urea bond, and a thiourea bond. A linear or branched alkylene group having 1 to 40 carbon atoms which may have any partial structure selected from the group and may have a substituent is more preferable. It may have a partial structure selected from the group consisting of an oxygen atom, a nitrogen atom, a hydrocarbon ring structure having 3 to 12 carbon atoms, an ester bond, a urethane bond, an amide bond, and a urea bond. It is more preferable that it is a linear or branched alkyl group having 1 to 40 carbon atoms which may have.
Here, the substituent introduced into G ¹ is preferably a hydroxyl group.

In the general formula (7), R ^{37 to} R ³⁹ each independently represent a hydrogen atom or a monovalent substituent, preferably a hydrogen atom or an alkyl group which may further have a substituent, and among them, R ³⁷ , R ³⁸ is particularly preferably a hydrogen atom, and R ³⁹ is particularly preferably a hydrogen atom or a methyl group.

R ^{40 to} R ⁴² each independently represents a hydrogen atom or a monovalent substituent, and specifically, a hydrogen atom, a halogen atom, a dialkylamino group, an alkoxycarbonyl group, a sulfo group, a nitro group, a cyano group, a substituted group An alkyl group which may further have a group, an aryl group which may further have a substituent, an alkoxy group which may further have a substituent, an aryloxy group which may further have a substituent, a substituent An alkylsulfonyl group which may further have a substituent, an arylsulfonyl group which may further have a substituent, and the like. Among them, a hydrogen atom, an alkoxycarbonyl group, an alkyl group which may further have a substituent, a substituent An aryl group which may further have a group is preferred.
Here, examples of the substituent that can be introduced include those listed in the general formula (6).

A ² in the general formula (7) represents —CO—, —C (═O) O—, —CONH—, —OC (═O) —, or a phenylene group, and in particular, —C (═O) O—. , -CONH-, and a phenylene group are preferable.

G ² represents a divalent organic group, and in its structure, an oxygen atom, a nitrogen atom, a sulfur atom, a hydrocarbon ring structure having 3 to 20 carbon atoms, an ester bond, a sulfonate ester bond, a phosphate ester bond, It may have any partial structure selected from the group consisting of a urethane bond, a thiourethane bond, an amide bond, a urea bond, and a thiourea bond, and may have a substituent. Are preferable in terms of performance such as strength and developability, and in the structure, oxygen atom, nitrogen atom, sulfur atom, hydrocarbon ring structure having 3 to 20 carbon atoms, ester bond, urethane bond, thiol Linear or branched carbon number which may have any partial structure selected from the group consisting of urethane bond, amide bond, urea bond and thiourea bond, and may have a substituent 1 to 40 alkyles The group preferably has a partial structure selected from the group consisting of an oxygen atom, a nitrogen atom, a hydrocarbon ring structure having 3 to 12 carbon atoms, an ester bond, a urethane bond, an amide bond, and a urea bond. It is more preferable that it is a linear or branched alkyl group having 1 to 40 carbon atoms which may have a substituent.
Here, the substituent in G ² is preferably a hydroxyl group.

Y ¹ represents an oxygen atom, a sulfur atom, —N (R ⁵³ ) — or a phenylene group which may have a substituent. Here, examples of R ⁵³ include a hydrogen atom and an alkyl group which may have a substituent.

In the general formula (8), R ^{43 to} R ⁴⁵ each independently represent a hydrogen atom or a monovalent substituent, and are preferably a hydrogen atom or an alkyl group which may have a substituent. Among them, R ⁴³ , R ⁴⁴ is particularly preferably a hydrogen atom, and R ⁴⁵ is particularly preferably a hydrogen atom or a methyl group.
R ^{46 to} R ⁵⁰ each independently represent a hydrogen atom or a monovalent substituent, for example, a hydrogen atom, a halogen atom, a dialkylamino group, an alkoxycarbonyl group, a sulfo group, a nitro group, a cyano group, or a substituent. An optionally substituted alkyl group, an aryl group that may further have a substituent, an alkoxy group that may further have a substituent, an aryloxy group that may further have a substituent, and a further substituent. And an alkylsulfonyl group which may further have a substituent, and the like. Among them, a hydrogen atom, an alkoxycarbonyl group, an alkyl group which may further have a substituent, and a substituent further The aryl group which may have is preferable. Examples of the substituent that can be introduced include those listed in the general formula (6).

A ³ in the general formula (8) represents —CO—, —C (═O) O—, —CONH—, —OC (═O) —, or a phenylene group, and in particular, —C (═O) O—. , -CONH-, and a phenylene group are preferable. Z ¹ represents an oxygen atom, a sulfur atom, or —N (R ⁵² ) —. As R ^{52, the same} as in general formula (6) can be mentioned.

G ³ represents a divalent organic group, and includes an oxygen atom, a nitrogen atom, a sulfur atom, a hydrocarbon ring structure having 3 to 20 carbon atoms, an ester bond, a sulfonate bond, and a phosphate bond in the structure. , Urethane bond, thiourethane bond, amide bond, urea bond, thiourea bond, any partial structure selected from the group consisting of, and optionally having a substituent, 3 to 3 carbon atoms It is preferably 20 alkylene groups in terms of performance such as strength and developability, and in the structure, an oxygen atom, a nitrogen atom, a sulfur atom, a hydrocarbon ring structure having 3 to 20 carbon atoms, an ester bond, a urethane bond, Linear or branched carbon that may have any partial structure selected from the group consisting of a thiourethane bond, an amide bond, a urea bond, and a thiourea bond, and may have a substituent Number 1-40 A ren group is more preferable, and the structure has a partial structure selected from the group consisting of an oxygen atom, a nitrogen atom, a hydrocarbon ring structure having 3 to 12 carbon atoms, an ester bond, a urethane bond, an amide bond, and a urea bond. It is more preferable that it is a linear or branched alkyl group having 1 to 40 carbon atoms which may have a substituent.
Here, the substituent in G ³ is preferably a hydroxyl group.

  As a method for synthesizing the specific graft polymer in the present invention, for example, (a) a resin in which a nitrogen-containing heterocycle and a carboxyl group are pendant is synthesized in advance, and glycidyl (meth) acrylate is added to the carboxyl group of the resin. , A method of reacting glycidyl group-containing unsaturated compounds such as allyl glycidyl ether and unsaturated alcohols such as allyl alcohol, 2-hydroxy acrylate, 2-hydroxy methacrylate, (b) a nitrogen-containing heterocycle and a hydroxyl group were previously pendant A method in which a resin is synthesized and a hydroxyl group of the resin is reacted with a free isocyanate group-containing unsaturated compound, an unsaturated acid anhydride, or an unsaturated acid halide, (c) a nitrogen-containing heterocyclic ring and an epoxy group A pendant resin is synthesized, and an unsaturated carbon is added to the epoxy group of the resin. A method of reacting an acid; (d) synthesizing a resin in which a specific functional group that gives an unsaturated group and a pendant nitrogen-containing heterocycle are generated in advance by base treatment, and subjecting the resin to base treatment As a typical example, a method of generating an unsaturated group in (1) can be given. Among these, from the viewpoint of synthesis stability and versatility, it is preferable to synthesize by the method (a), (b) or (d), and it is more preferable to synthesize by the method (d).

  Here, the monomer used in the synthesis by the method (d), which is a structural unit in which an ethylenically unsaturated double bond is pendant by elimination reaction, includes “(meth) acryloyl group, Or, a monomer having the same structure as “a structure in which an acid is added to an ethylenically unsaturated bond part of a styryl group” is preferably used. Among them, monomers having partial structures of the following general formulas (9) to (12) are preferably used. preferable.

In General Formula (9) and General Formula (10), R ^{a to} R ^d each independently represent a hydrogen atom or a monovalent substituent.
The “monovalent substituent” represented by R ^{a to} R ^d may be any group that can be substituted on the benzene ring in general formula (9) and general formula (10).
Preferred monovalent substituents represented by R ^{a to} R ^d include aliphatic groups, aromatic groups, heterocyclic groups, halogen atoms, hydroxyl groups, thiol groups, cyano groups, nitro groups, (meth) acryloyl groups. Carboxy group, amino group, aliphatic amino group, aromatic amino group, heterocyclic amino group, aliphatic oxy group, aromatic oxy group, heterocyclic oxy group, aliphatic thio group, aromatic thio group, aliphatic sulfone Amide group, aromatic sulfonamido group, acyl group, aliphatic oxycarbonyl group, aliphatic oxycarbonylamino group, aromatic oxycarbonylamino group, aliphatic thiocarbonylamino group, aromatic thiocarbonylamino group, aliphatic aminocarbonyl Amino group, aromatic aminocarbonylamino group, carbamoyl group, aliphatic sulfonyl group, aromatic sulfonyl group, silyl group, aliphatic Xylyl group, silyloxy group, aliphatic carbonyloxy group, aromatic carbonyloxy group, heterocyclic carbonyloxy group, aliphatic oxycarbonyloxy group, aliphatic sulfonyloxy group, sulfamoyl group, sulfo group, phosphonyl group, or phosphone group Can be mentioned.

  In particular, from the viewpoint of sensitivity and solubility, aliphatic groups, aromatic groups, heterocyclic groups, halogen atoms, hydroxyl groups, thiol groups, (meth) acryloyl groups, carboxy groups, amino groups, aliphatic amino groups, aromatics Amino group, aliphatic oxy group, aromatic oxy group, heterocyclic oxy group, aliphatic thio group, aliphatic sulfonamido group, aliphatic oxycarbonyl group, aliphatic oxycarbonylamino group, silyl group, aliphatic oxysilyl group, An aliphatic carbonyloxy group, an aliphatic oxycarbonyloxy group, an aliphatic sulfonyloxy group, a sulfo group, or a phosphone group is preferred.

The aliphatic group represented by R ^{a to} R ^d means an alkyl group, an alkenyl group, or an alkynyl group. The aliphatic group may have a branch and may form a ring. Moreover, it may be unsubstituted or may have a substituent. When the aliphatic group has a substituent, it can have the various substituents mentioned in the description of the “monovalent substituent”, and when it has two or more substituents, the substituents are the same. Or different. When the aliphatic group is an alkyl group, it may be linear, branched, or may form a ring, and preferably has 1 to 21 carbon atoms, It is more preferable that it is C1-C16, and it is especially preferable that it is C1-C12.

  Among the alkyl groups having 1 to 21 carbon atoms, methyl group, ethyl group, n-propyl group, n-butyl group, n-amyl group, n-hexyl group, n-heptyl group, n-octyl group, n- Nonyl group, n-decyl group, i-propyl group, sec-butyl group, i-butyl group, t-butyl group, 1-methylbutyl group, 1-ethylpropyl group, 2-methylbutyl group, i-amyl group, neopentyl Group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, t-amyl group, 1,3-dimethylbutyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, 2-ethyl-2- Methylpropyl group, linear or branched heptyl group, 1-methylheptyl group, 2-ethylhexyl group, 1,5-dimethylhexyl group, t-octyl group, branched nonyl group, branched decyl group, cyclo Propyl, cyclopropylmethyl, cyclobutyl, cyclobutylmethyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, cycloheptyl, cyclooctyl, cyclohexylpropyl, cyclododecyl, norbornyl, bornyl, noradamantyl A group, an adamantyl group, an adamantylmethyl group, a 1- (1-adamantyl) ethyl group, a 3,5-dimethyladamantyl group, a cyclopentylethyl group, or a bicyclooctyl group is preferred.

  Among the alkyl groups exemplified above, an alkyl group substituted with fluorine is also particularly suitable. Examples of the fluorine-substituted alkyl group include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a nonafluorobutyl group. , A tridecafluorohexyl group and a pentadecafluoroheptyl group are preferable, and a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a nonafluorobutyl group, and a tridecafluorohexyl group are particularly preferable.

  When the aliphatic group is an alkenyl group, it may be unsubstituted or may have a substituent, and an alkenyl group having 2 to 21 carbon atoms is preferable. A C2-C16 alkenyl group is more preferable, and a C2-C10 alkenyl group is still more preferable. Examples of the alkenyl group having 2 to 21 carbon atoms include a vinyl group, isopropenyl group, 2-propenyl group, 2-methyl-propenyl group, 1-methyl-1-propenyl group, 1-butenyl group and 3-butenyl group. 1-methyl-1-butenyl group, 1,1-dimethyl-3-butenyl group, 1-pentenyl group, 2-pentenyl group, 1-ethyl-1-pentenyl group, 1-hexenyl group, 1-heptenyl group, 1-cyclopentenyl group, 2-cyclopentenylmethyl group, cyclohexenyl group, 1-methyl-2-cyclohexenyl group, 1,4-dihydro-2-methylphenyl group are more preferable, and vinyl group, isopropenyl group are more preferable. 2-propenyl group, 2-methyl-propenyl group, 1-methyl-1-propenyl group, 1-butenyl group, 3-butenyl group, 1-methyl-1-but Nyl group, 1,1-dimethyl-3-butenyl group, 1-pentenyl group, 2-pentenyl group, 1-ethyl-1-pentenyl group, 1-hexenyl group, 1-cyclopentenyl group, 2-cyclopentenylmethyl group , A cyclohexenyl group, a 1-methyl-2-cyclohexenyl group, and a 1,4-dihydro-2-methylphenyl group are preferable.

The aromatic group represented by R ^{a to} R ^d means an aryl group. The aryl group may be unsubstituted or may have a substituent, and preferably has 6 to 21 carbon atoms. Especially, a C6-C15 aryl group is preferable and a C6-C10 aryl group is more preferable.
Preferred examples of the aryl group having 6 to 21 carbon atoms include a phenyl group, a naphthyl group, a biphenylenyl group, an acenaphthenyl group, a fluorenyl group, an anthracenyl group, an anthraquinonyl group, and a pyrenyl group. Group, naphthyl group, biphenylenyl group, acenaphthenyl group, fluorenyl group or anthracenyl group is more preferable, and further, phenyl group, naphthyl group, biphenylenyl group or fluorenyl group is particularly preferable.
The aryl group is preferably a phenyl group or a naphthyl group, and particularly preferably a phenyl group.

The hetero ring represented by R ^{a to} R ^d has a hetero atom (for example, a nitrogen atom, a sulfur atom, an oxygen atom) in the ring, and is a saturated ring or an unsaturated ring. It may be a single ring or a condensed ring, and may be unsubstituted or may have a substituent. It is preferable that carbon number of a heterocyclic ring is 1-32, and 2-16 are more preferable. For example, isocyanuric ring, epoxy ring, furan ring, tetrahydrofuran ring, pyran ring, tetrahydropyran ring, tetrahydrothiophene ring, thiophene ring, pyrrolidine ring, piperidine ring, piperazine ring, morpholine ring, thiomorpholine ring, pyrrole ring, pyrazole ring, Imidazole ring, triazole ring, oxazole ring, thiazole ring, thiadiazole ring, indole ring, carbazole ring, benzofuran ring, pyridine ring, quinoline ring, pyrimidine ring, pyridazine ring, pyrazine ring, uracil ring, lactone ring, particularly isocyanuric ring , Epoxy ring, tetrahydrofuran ring, tetrahydropyran ring, tetrahydrothiophene ring, pyrrolidine ring, piperidine ring, morpholine ring, pyrrole ring, pyrazole ring, imidazole ring, triazole ring, Kisazoru ring, a thiazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a lactone ring.

In general formula (9), and ^{Z 2} in the general formula (11), and the general formula (10), and ^{Z 3} in the general formula (12) represents an anionic leaving group.
In the general formula (11) and the general formula (12), R ^{61 to} R ⁶³ each independently represents a hydrogen atom or a monovalent organic group. Preferable examples are the same as R ^{6l to} R ⁶³ in the following general formula (13) and general formula (14).

  In the present invention, examples of the most preferable monomer among the monomers having a structure that generates an ethylenically unsaturated double bond by elimination reaction include the following general formula (13), general formula (14), or general formula: The radically polymerizable compound represented by (15) is mentioned.

In the general formula (13) and the general formula (14), R ^{61 to} R ⁶³ each independently represent a hydrogen atom or a monovalent substituent. ^Examples of R ⁶¹ include a hydrogen atom or an alkyl group which may have a substituent. Among them, a hydrogen atom, a methyl group, a methylalkoxy group, and a methyl ester group are preferable.

R ⁶² and R ⁶³ may each independently have a hydrogen atom, a halogen atom, an amino group, a dialkylamino group, a carboxyl group, an alkoxycarbonyl group, a sulfo group, a nitro group, a cyano group, or a substituent. Alkyl group, aryl group which may have a substituent, alkoxy group which may have a substituent, aryloxy group which may have a substituent, alkylamino group which may have a substituent, substituted An arylamino group that may have a group, an alkylsulfonyl group that may have a substituent, an arylsulfonyl group that may have a substituent, and the like, among them, a hydrogen atom, a carboxyl group, an alkoxycarbonyl group An alkyl group which may have a substituent and an aryl group which may have a substituent are preferable.
Here, examples of the substituent that can be introduced include a methoxycarbonyl group, an ethoxycarbonyl group, an isopropyloxycarbonyl group, a methyl group, an ethyl group, and a phenyl group.

In the general formula (13), R ⁶⁴ represents a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, —COOH, —CN, —CF ₃ , —CH ₂ OH, —CH ₂ COOH, —CH ₂ COOR ′. Or —COOR ″. Examples of the hydrocarbon group having 1 to 6 carbon atoms represented by R ′ or R ″ include a methyl group, an ethyl group, a propyl group, a butyl group, and a hexyl group. A methyl group and an ethyl group are preferred. Among these, R ⁶⁴ is preferably a hydrogen atom, a methyl group, —COOH, —CN, —CF ₃ , —CH ₂ OH, or —CH ₂ COOH, and more preferably a hydrogen atom or a methyl group.
Q represents an oxygen atom, —NH—, or —NR ⁰¹ — (wherein R ⁰¹ represents an alkyl group which may have a substituent).

A ⁴ represents an n ⁴ +1 valent linking group. Although not particularly limited, preferably, in the structure, an oxygen atom, a nitrogen atom, a sulfur atom, a hydrocarbon ring structure having 3 to 20 carbon atoms, a heterocycle, an ester bond, a sulfonate bond, a phosphate bond, a urethane It is preferably an alkyl group having 2 to 60 carbon atoms or an aryl group which may have an atom or a partial structure selected from the group consisting of a bond, a thiourethane bond, an amide bond, a urea bond, and a thiourea bond. In the structure, oxygen atom, nitrogen atom, sulfur atom, hydrocarbon ring structure having 3 to 20 carbon atoms, ester bond, urethane bond, thiourethane bond, amide bond, urea bond, and thiourea bond A linear or branched alkyl group having 1 to 40 carbon atoms which may have an atom or a partial structure selected is more preferable. Linear or branched carbon number 1 which may have an atom or a partial structure selected from the group consisting of an atom, a hydrocarbon ring structure having 3 to 12 carbon atoms, an ester bond, a urethane bond, and an amide bond More preferred is an alkyl group of ˜40.

The n ⁴ +1 valent linking group represented by A ⁴ may further have a substituent if it can be introduced. As the substituent that can be introduced, a chain, branched or cyclic alkyl group having 1 to 10 carbon atoms is preferable from the viewpoint of availability of raw materials, and from the viewpoint of sensitivity and developability, a hydroxy group, a mercapto group, A group having an ethylenically unsaturated bond is preferred. Further, a hydroxy group is most preferable from the viewpoint of balance between sensitivity and developability. n ⁴ represents an integer of 1 to 10.

Furthermore, X ⁴ represents -G ¹ -X ^5- , wherein G ¹ represents a divalent organic group linked to A ^4, and X ⁵ represents an oxygen atom, a sulfur atom, or -NR ^03. — (Wherein R ⁰³ represents a hydrogen atom or an alkyl group which may have a substituent).
In addition, Z ² represents an anionic leaving group.

In the general formula (14), R ⁶⁵ and R ⁶⁶ each independently represent a hydrogen atom or a monovalent organic group.
Here, the monovalent organic group represented by R ^65, and R ^66, include such hydrocarbon group having 1 to 6 carbon atoms, among them, a methyl group, an ethyl group, a phenyl group is preferable.
In the general formula ^{(14), R 67} has the same meaning as ^{R 64} in the formula (13), and preferred examples are also the same.

Moreover, ^{A 5} is ^-G 2 -X ⁶ - represents, ^{wherein, G} 2 represents a divalent organic group linked with ^{G 4, X 6} represents an oxygen atom, a sulfur atom, or ^{-NR 03} — (Wherein R ⁰³ represents a hydrogen atom or an alkyl group which may have a substituent).
A ⁶ represents an oxygen atom, a sulfur atom, or —NR ⁰⁴ — (wherein R ⁰⁴ represents a hydrogen atom or an alkyl group which may have a substituent).

In addition, G ⁴ represents an n ⁵ +1 valent linking group. Although not particularly limited, preferably, in the structure, an oxygen atom, a nitrogen atom, a sulfur atom, a hydrocarbon ring structure having 3 to 20 carbon atoms, a heterocycle, an ester bond, a sulfonate bond, a phosphate bond, a urethane It is preferably an alkyl or aryl group having 2 to 60 carbon atoms, which may have an atom or a partial structure selected from the group consisting of a bond, a thiourethane bond, an amide bond, a urea bond, and a thiourea bond, In the structure, selected from the group consisting of oxygen atom, nitrogen atom, sulfur atom, hydrocarbon ring structure having 3 to 20 carbon atoms, ester bond, urethane bond, thiourethane bond, amide bond, urea bond, and thiourea bond Is more preferably a linear or branched alkyl group having 1 to 40 carbon atoms, which may have an atom or a partial structure, in which oxygen atom, nitrogen A linear or branched carbon number 1 which may have an atom or a partial structure selected from the group consisting of a C 3-12 hydrocarbon ring structure, an ester bond, a urethane bond, and an amide bond More preferred is an alkyl group of ˜40.

The n ⁵ +1 valent linking group represented by G ⁴ may further have a substituent when it can be introduced. As the substituent that can be introduced, a chain, branched or cyclic alkyl group having 1 to 10 carbon atoms is preferable from the viewpoint of availability of raw materials, and from the viewpoint of sensitivity and developability, a hydroxy group, a mercapto group, A group having an ethylenically unsaturated bond is preferred. Further, a hydroxy group is most preferable from the viewpoint of balance between sensitivity and developability. n ⁵ represents an integer of 1 to 10.
Z ³ represents an anionic leaving group.

In the general formula (15), R ^{68 to} R ⁷² each independently represent a hydrogen atom or a monovalent substituent, and at least one of them is represented by the following general formula (16) or general formula (17). It is a group represented.
R ^{73 to} R ⁷⁵ each independently represent a hydrogen atom or a monovalent organic group. Here, examples of the monovalent organic group represented by R ^{73 to} R ⁷⁵ include a hydrocarbon group having 1 to 6 carbon atoms, and among them, a methyl group, an ethyl group, and a phenyl group are preferable.

In the general formula (16), G ⁵ represents an m ⁴ +1 valent linking group, and examples include the examples of the linking group described in G ⁴ in the general formula (14), and preferable examples include G ^4. It is the same. m ⁴ represents an integer of 1 to 10.
Moreover, the general formula ^R 61 ^{to R} 63 in (16), ^{Z 3,} and ^{A 5, R} 61 ^~R 63, ^{Z 3} in Formula (14), and ^{A 5} as synonymous.

In the general formula (17), G ⁶ represents an m ⁵ +1 valent linking group, and examples thereof include the examples of the linking group described in A ⁴ in the general formula (13), and preferable examples include A ^4. It is the same. m ⁵ represents an integer of 1 to 10.
In general ^R 61 ^{to R} 63 in formula (17), ^{Z 2,} and ^{A 4} have the same meaning as ^R 61 ^~R 63, ^{Z 2,} and ^{A 4} in the general formula (13).

  Specific examples (13-1) to (13-12) of the radical polymerizable compound represented by the general formula (13) are shown below, but the present invention is not limited thereto.

  Specific examples [i-1 to i-60] of the radical polymerizable compound represented by the general formula (14) and the radical polymerizable compound represented by the general formula (15) are shown, but the present invention is limited to these. Is not to be done.

The structural unit in which the ethylenically unsaturated double bond is pendant in the present invention includes (13-1), (13-7), (13-8), i-1, i-2, i-6, i. -10, i-15, i-31, i-33, i-48 and i-49 are preferred.
The ratio of the structural unit in which the ethylenically unsaturated double bond is pendant in the specific graft polymer is preferably 35% by mass to 95% by mass, more preferably 37% by mass to 90% by mass, and 40% by mass to 85% by mass. Is most preferred.

  In the pigment dispersion composition of the present invention, the content of (A) the specific graft polymer is preferably a mass ratio of pigment: specific graft polymer = 1: 0.1 to 1: 2, more preferably 1: It is 0.2-1: 1, More preferably, it is 1: 0.4-1: 0.7. The effect of the acrylic acid of the present invention appears remarkably when pigment: specific graft polymer = 1: 0.4 to 1: 0.55.

  The content of the specific graft polymer (A) in the pigment dispersion composition of the present invention is preferably 1 to 50% by mass, and 3 to 40% by mass in the total solid content of the pigment dispersion composition. More preferred.

Further, in order to improve the high color reproducibility of the liquid crystal display device and to improve the color separation property of the solid-state imaging device, it is necessary that the pigment concentration is high. Especially effective with objects. More specifically, the value obtained by dividing the total mass of the polymer compound contained in the pigment dispersion composition by the total mass of (B) pigment and pigment derivative described later is in the range of 0.2 to 0.55. However, it is preferably in the range of 0.3 to 0.4.
Even when the amount of the polymer compound is small, the dispersibility of the pigment is good, the dispersion stability is good, and when the colored curable composition is made, the re-dissolvability of the dry film in the solvent is good. Thus, it is possible to provide a pigment dispersion composition with little residue during development.

<(B) Pigment>
The pigment dispersion composition of the present invention contains a pigment. The pigment used here has a higher contrast as a color filter as its particle size is smaller. In particular, when a pigment having a particle size of 10 to 25 nm is dispersed with the specific graft polymer of the present invention, it can be dispersed well and the contrast is improved. In addition, since the pigment of this size is fine, there is a problem that the pigment aggregates and the viscosity is improved when the pigment dispersion is stored for a long time under high temperature and high humidity. This problem can be solved by using the introduced graft type dispersant.
When the particle diameter of the pigment is within the above range, the transmittance is high, the color characteristics are good, and it is effective for forming a color filter with high contrast.
The average primary particle diameter is obtained by observing with an SEM or TEM, measuring 100 particle sizes in a portion where the particles are not aggregated, and calculating an average value.

  Further, the pigment concentration of the colored curable composition is usually 30% by weight or less, but in recent years, a higher pigment concentration is required. When the pigment concentration is increased, components that contribute to image forming properties, such as an additive resin that imparts solubility in an alkaline developer, are relatively reduced, resulting in a problem that the image forming performance originally possessed is lost. .

When the specific graft polymer of the present invention is used as a dispersant, it can be used in a high pigment concentration region because it is sufficiently solubilized in the developer without adding another resin in order to dissolve in the alkaline developer. In addition, since the specific graft polymer has dispersion stability, it has a characteristic that a fine pigment can be used at a high pigment concentration.
The pigment concentration can be used in the range of 10 to 55% by mass, but the effect is particularly remarkable in the high pigment concentration region in the range of 35 to 55% by mass and in the range of 40 to 55% by mass.

The pigment dispersion composition of the present invention contains at least one (B) pigment in an organic solvent.
As the pigment that can be used in the pigment dispersion composition of the present invention, conventionally known various inorganic pigments or organic pigments can be used. Moreover, considering that it is preferable that the pigment has a high transmittance regardless of whether it is an inorganic pigment or an organic pigment, it is preferable to use a pigment having a particle size as small as possible, and considering handling properties. Then, a pigment having an average primary particle diameter of 10 to 25 nm is preferable.

  Examples of the inorganic pigment include metal compounds represented by metal oxides, metal complex salts, and the like. Specifically, iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony And metal oxides such as the above, and complex oxides of the above metals.

Examples of the organic pigment include pigments described in paragraphs [0201] to [0204] of JP-A-2009-20453.
These organic pigments can be used alone or in various combinations in order to increase color purity. Specific examples of the above combinations are shown below. For example, as a red pigment, an anthraquinone pigment, a perylene pigment, a diketopyrrolopyrrole pigment alone or at least one of them and a disazo yellow pigment, an isoindoline yellow pigment, a quinophthalone yellow pigment, Alternatively, as the red pigment, a mixture of at least one of an anthraquinone pigment, a perylene pigment, a diketopyrrolopyrrole pigment and a perylene red pigment, an anthraquinone red pigment, a diketopyrrolopyrrole red pigment, or the like is used. be able to. For example, as an anthraquinone pigment, C.I. I. Pigment Red 177, and perylene pigments include C.I. I. Pigment red 155, C.I. I. Pigment Red 224, and diketopyrrolopyrrole pigments include C.I. I. Pigment Red 254, red pigments in terms of color reproducibility, and C.I. I. Pigment yellow 83, C.I. I. Pigment yellow 139 or C.I. I. Mixing with Pigment Red 177 is preferred. The mass ratio of the red pigment to the other pigment (red pigment; other pigment) is preferably 100: 5 to 100: 80. If the content of the other pigment is 100: 4 or less with respect to the red pigment, it may be difficult to suppress the light transmittance from 400 nm to 500 nm and the color purity may not be increased. Further, when the content of other pigments is 100: 81 or more with respect to the red pigment, the coloring power may be lowered. Particularly, the mass ratio is optimally in the range of 100: 10 to 100: 65. In the case of a combination of red pigments, it can be adjusted in accordance with the chromaticity.

  Further, as the green pigment, one kind of halogenated phthalocyanine pigment can be used alone or a mixture thereof with a disazo yellow pigment, a quinophthalone yellow pigment, an azomethine yellow pigment or an isoindoline yellow pigment can be used. . For example, C.I. I. Pigment Green 7, 36, 37 and C.I. I. Pigment yellow 83, C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, C.I. I. Pigment yellow 180 or C.I. I. Mixing with Pigment Yellow 185 is preferred. The mass ratio of green pigment to yellow pigment (green pigment: yellow pigment) is preferably 100: 5 to 100: 200. If the content of the green pigment is less than 100: 5 by mass with respect to the yellow pigment, it may be difficult to suppress the light transmittance of 400 to 450 nm, and the color purity may not be increased. Further, when the content of the green pigment exceeds 100: 200 with respect to the yellow pigment, the dominant wavelength tends to be closer to the longer wavelength, and the deviation from the NTSC target hue may increase. The mass ratio is particularly preferably in the range of 100: 20 to 100: 150.

As the blue pigment, a single phthalocyanine pigment or a mixture of this and a dioxazine purple pigment can be used. As a particularly preferred example, C.I. I. Pigment blue 15: 6 and C.I. I. A mixture with pigment violet 23 can be mentioned.
The mass ratio of blue pigment to purple pigment (blue pigment: purple pigment) is preferably 100: 0 to 100: 100, more preferably 100: 70 or less.

Moreover, as a pigment suitable for black matrix use, carbon black, graphite, titanium black, iron oxide, titanium oxide alone or a mixture thereof can be used, and a combination of carbon black and titanium black is preferable.
The mass ratio of carbon black to titanium black (carbon black: titanium black) is preferably in the range of 100: 0 to 100: 60. When the mass ratio of titanium black to carbon black is 100: 61 or more, dispersion stability may be lowered.

(Pigment processing)
It is preferable to use the pigment of the present invention that has been subjected to a refinement treatment in advance. The finer primary particles of the pigment are well known by mechanically kneading with i) a pigment, ii) a water-soluble inorganic salt, and iii) a water-soluble organic solvent that does not substantially dissolve the inorganic salt with a kneader. (Salt milling method). In this step, if necessary, iv) a pigment-coated polymer compound, v) a pigment derivative, etc. may be used simultaneously.

i) Examples of the pigment include the same pigments as described above.
ii) The water-soluble inorganic salt is not particularly limited as long as it is soluble in water, and sodium chloride, barium chloride, potassium chloride, sodium sulfate, and the like can be used. Sodium is preferably used. Ii) The amount of the water-soluble inorganic salt used for salt milling is preferably 1 to 30 times by weight, particularly 5 to 25 times by weight of the organic pigment, in terms of both processing efficiency and production efficiency. ii) The water content in the water-soluble inorganic salt is preferably 1% or less. i) The finer efficiency is higher as the amount ratio of the water-soluble inorganic salt to the organic pigment is larger, but the processing amount of the pigment is reduced once.

  iii) A small amount of the water-soluble organic solvent that does not substantially dissolve the inorganic salt is one that functions to wet the i) organic pigment, ii) the water-soluble inorganic salt, and is dissolved (mixed) in water. And if it does not melt | dissolve the inorganic salt to be used substantially, it will not specifically limit. However, a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety because the temperature rises during salt milling and the solvent easily evaporates. Examples of the water-soluble organic solvent include 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, ethylene glycol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monoethyl ether. Acetate, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol Monoethyl ether, liquid polypropylene glycol or the like is used.

  However, if it is adsorbed to the pigment by using a small amount and does not flow away into the wastewater, benzene, toluene, xylene, ethylbenzene, chlorobenzene, nitrobenzene, aniline, pyridine, quinoline, tetrahydrofuran, dioxane, ethyl acetate, isopropyl acetate, butyl acetate, hexane , Heptane, octane, nonane, decane, undecane, dodecane, cyclohexane, methylcyclohesasan, halogenated hydrocarbon, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, etc. Two or more kinds of solvents may be mixed and used as necessary.

  iii) The addition amount of the water-soluble organic solvent is preferably 5 to 50 parts by weight with respect to 100 parts by weight of the water-soluble inorganic salt. More preferably, it is 10 to 40 parts by weight, and optimally 15 to 35 parts by weight. When the addition amount is less than 5 parts by weight, uniform kneading becomes difficult and the particle size may become uneven. When the addition amount is 50 parts by weight or more, the kneaded composition becomes too soft, and it becomes difficult to apply shear to the kneaded composition, so that a sufficient refinement effect may not be obtained.

iii) The water-soluble organic solvent may be added in the initial stage of salt milling, or may be added separately. iii) The water-soluble organic solvent may be used alone or in combination of two or more.
Although there is no particular limitation on the operating conditions of the wet pulverizing apparatus in the present invention, the operating conditions in the case where the apparatus is a kneader are as follows. 200 rpm is preferable, and a relatively large biaxial rotation ratio is preferable because the grinding effect is large. The operation time is preferably 1 to 8 hours in combination with the dry grinding time, and the internal temperature of the apparatus is preferably 50 to 150 ° C. Further, the water-soluble inorganic salt that is a pulverization medium preferably has a pulverization particle size of 5 to 50 μm, a sharp particle size distribution, and a spherical shape.

  iv) The pigment-coated polymer compound is preferably a solid at room temperature, water-insoluble, and iii) at least partially soluble in a water-soluble organic solvent used as a wetting agent during salt milling. , Modified natural resin, synthetic resin, synthetic resin modified with natural resin, or (A) specific graft polymer according to the present invention, and in particular, (A) specific graft polymer of the present invention can be used. It is preferable to use it.

When using a dried treated pigment, the compound used is preferably solid at room temperature. The natural resin is typically rosin, and the modified natural resin includes rosin derivatives, fiber derivatives, rubber derivatives, protein derivatives and oligomers thereof. Examples of the synthetic resin include epoxy resin, acrylic resin, maleic acid resin, butyral resin, polyester resin, melamine resin, phenol resin, polyurethane resin, and the like. Examples of the synthetic resin modified with a natural resin include rosin-modified maleic resin and rosin-modified phenol resin.
Synthetic resins include polyamidoamine and its salt, polycarboxylic acid and its salt, high molecular weight unsaturated acid ester, polyurethane, polyester, poly (meth) acrylate, (meth) acrylic copolymer, naphthalenesulfonic acid formalin condensate Is mentioned.
(A) As the specific graft polymer, the above-described polymer compounds can be used.
The timing of adding these resins may be added all at the beginning of salt milling, or may be added in divided portions.
v) Examples of the pigment derivative include the same pigment derivatives as described later.

<Pigment derivative>
A pigment derivative is added to the pigment dispersion composition of the present invention as necessary. The pigment is dispersed in the colored curable composition as fine particles by adsorbing the pigment derivative having a part having an affinity for the dispersant or a polar group to the pigment surface and using it as the adsorption point of the dispersant. Therefore, the reaggregation can be prevented, and it is effective for constructing a color filter having high contrast and excellent light transmittance.

  Specifically, the pigment derivative is a compound in which an organic pigment is used as a base skeleton, and an acidic group, a basic group, or an aromatic group is introduced into a side chain as a substituent. Specific examples of organic pigments include quinacridone pigments, phthalocyanine pigments, azo pigments, quinophthalone pigments, isoindoline pigments, isoindolinone pigments, quinoline pigments, diketopyrrolopyrrole pigments, and benzimidazolone pigments. Is mentioned. In general, light yellow aromatic polycyclic compounds such as naphthalene series, anthraquinone series, triazine series and quinoline series which are not called pigments are also included. Examples of the dye derivative include JP-A-11-49974, JP-A-11-189732, JP-A-10-245501, JP-A-2006-265528, JP-A-8-295810, and JP-A-11-199796. JP, 2005-234478, JP 2003-240938, JP 2001-356210, etc. can be used.

  As content in the pigment dispersion composition of the pigment derivative based on this invention, 1-30 weight part is preferable with respect to 100 weight part of pigments, and 3-20 weight part is more preferable. When the content is within the above range, the dispersion can be favorably performed while the viscosity is kept low, the dispersion stability after dispersion can be improved, and the color characteristics with high transmittance can be obtained. When producing a filter, it can be configured to have high contrast with good color characteristics.

  The timing of adding the pigment derivative may be added during salt milling or may be added during dispersion. It may be added to both during salt milling and dispersion.

  The dispersion method is, for example, using a bead disperser using zirconia beads or the like (for example, a disperse mat made by GETZMANN Co., Ltd.) that has been previously mixed with a pigment and a dispersant and previously dispersed with a homogenizer or the like. This can be done by fine dispersion. The dispersion time is preferably about 3 to 6 hours.

<Dispersant>
The pigment dispersion composition of the present invention contains at least one dispersant. With this dispersant, the dispersibility of the pigment can be improved.
As the dispersant, it is necessary to use at least the above-mentioned (A) specific graft polymer. As a result, the dispersion state of the pigment in the organic solvent is improved, and, for example, when a color filter is configured using the pigment dispersion composition of the present invention, high developability even when the pigment is contained at a high concentration. Surface smoothness can be expressed.
(A) When the specific graft polymer is used as a dispersant, the above-described polymer compound can be used.

  If necessary, conventionally known dispersants such as pigment dispersants and surfactants, and other components can be added.

Known dispersants (pigment dispersants) include polymer dispersants such as polyamidoamines and salts thereof, polycarboxylic acids and salts thereof, high molecular weight unsaturated acid esters, modified polyurethanes, modified polyesters, and modified poly (meth). Acrylate, (meth) acrylic copolymer, naphthalenesulfonic acid formalin condensate], polyoxyethylene alkyl phosphate ester, polyoxyethylene alkylamine, alkanolamine, pigment derivative, and the like.
The polymer dispersant can be further classified into a linear polymer, a terminal-modified polymer, a graft polymer, and a block polymer according to the structure.

  The ratio of the pigment-coated polymer compound and the dispersant is not particularly limited. However, when the dispersant is a polymer dispersant, 10/90 to 90/10 is preferable, and 20/80 to 80/20 is more preferable. preferable.

<(C) Organic solvent>
The solvent in the pigment dispersion composition of the present invention is not particularly limited as long as it is an organic solvent, and can be appropriately selected from known solvents such as 1-methoxy-2-propyl acetate and 1-methoxy-2. -(Poly) alkylene glycol monoalkyl ethers such as propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether and their acetates; Acetates such as ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate and i-butyl acetate; aromatic hydrocarbons such as benzene, toluene and xylene; Ethyl ketone, acetone, methyl isobutyl ketone and cyclohexanone; ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, diethylene glycol, alcohols such as glycerin, and the like. These may be used individually by 1 type and may use 2 or more types together. Among these, alkylene glycol monoalkyl ethers and their acetates, acetates, methyl ethyl ketone, and the like are preferable.

The content of the solvent in the pigment dispersion composition is appropriately selected according to the use of the pigment dispersion composition. When the pigment dispersion composition is used for the preparation of a colored curable composition to be described later, from the viewpoint of handleability, it should be contained so that the solid content concentration including the pigment and the pigment dispersant is 5 to 50% by mass. Can do.
(C) It is preferable to have 10% by mass or more of 1-methoxy-2-propyl acetate as the organic solvent.

  A preferred embodiment of the pigment dispersion composition of the present invention is a pigment dispersion obtained by dispersing a processed pigment coated with a polymer compound having a weight average molecular weight of 1,000 or more, a pigment derivative, and a dispersant in an organic solvent. It is a composition. (A) The specific graft polymer may be used as a pigment-coated polymer compound added at the time of pigment processing, or may be used as a dispersant, or both of the independent (A) specific graft polymers may be used. However, it is preferably used as a dispersant.

  In the case of a polymer dispersant, the addition amount of the dispersant is preferably 0.5 to 100% by mass, more preferably 3 to 100% by mass, and more preferably 5 to 80% by mass with respect to the pigment. % Is particularly preferred. When the amount of the pigment dispersant is within the above range, a sufficient pigment dispersion effect can be obtained. However, the optimum addition amount of the dispersant is appropriately adjusted depending on the combination of the type of pigment used, the type of solvent, and the like.

-Preparation of pigment dispersion composition-
The preparation mode of the pigment dispersion composition of the present invention is not particularly limited. For example, the pigment, the pigment dispersant, and the solvent are mixed using a vertical or horizontal sand grinder, a pin mill, a slit mill, an ultrasonic disperser, or the like. It can be obtained by performing fine dispersion treatment with beads made of glass, zirconia or the like having a particle diameter of 0.01 to 1 mm.

  Before performing bead dispersion, knead and disperse using a two-roll, three-roll, ball mill, tron mill, disper, kneader, kneader, homogenizer, blender, single- or twin-screw extruder while applying strong shearing force. It is also possible to perform processing.

  For details on kneading and dispersing, see T.W. C. “Paint Flow and Pigment Dispersion” by Patton (published by John Wiley and Sons, 1964) and the like.

  The pigment dispersion composition of the present invention is suitably used for a colored curable composition used for producing a color filter.

[Colored curable composition]
The colored curable composition of the present invention comprises the above-described pigment dispersion composition of the present invention, (D) a polymerizable compound, and (E) a photopolymerization initiator, and if necessary, an alkali-soluble resin. And other components may be included. Hereinafter, each component will be described in detail.

  The pigment concentration of the colored curable composition of the present invention (mass% of the pigment in the total solid content of the colored curable composition) is preferably 35% by mass to 90% by mass, and more preferably 40% by mass to 80% by mass. preferable. The present invention is particularly effective when the pigment concentration is high, dispersibility of the pigment is high, and when it is made a colored curable composition, it exhibits dispersion stability that cannot be achieved by conventional techniques, and is a solvent for a dry film. It is possible to provide a colored curable composition having high solubility and less residue on the substrate when developed.

(D) Polymerizable compound As the polymerizable compound, a compound having at least one addition-polymerizable ethylenically unsaturated group and having a boiling point of 100 ° C. or higher at normal pressure is preferable. Is more preferable.

Specific examples of the compound having at least one addition-polymerizable ethylenically unsaturated group and having a boiling point of 100 ° C. or higher at normal pressure include, for example, paragraph No. of JP-A-2008-233244. [0115] to [0116].
Of these, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and a structure in which these acryloyl groups are via ethylene glycol and propylene glycol residues are preferable. These oligomer types can also be used.
In addition, ethylenically unsaturated compounds having an acid group are also suitable. Examples of commercially available products include TO-756, which is a carboxyl group-containing trifunctional acrylate manufactured by Toagosei Co., Ltd., and a carboxyl group-containing pentafunctional acrylate. Some TO-1382 and the like can be mentioned.

(D) A polymeric compound can be used in combination of 2 or more types in addition to being used alone.
(D) As content in the colored curable composition of a polymeric compound, 3-55 mass% is preferable in the total solid of this composition, More preferably, it is 10-50 mass%. When the content of the polymerizable compound is within the above range, the curing reaction can be sufficiently performed.

(E) Photopolymerization initiator Examples of the photopolymerization initiator include the compounds described in paragraphs [0098] to [0112] of JP-A-2008-81732.
These photopolymerization initiators may be used alone or in combination of two or more.
As content in the colored curable composition of a photoinitiator, 0.1-10.0 mass% is preferable in the total solid of this composition, More preferably, it is 0.5-5.0 mass%. It is. When the content of the photopolymerization initiator is within the above range, the polymerization reaction can proceed well to form a film with good strength.

<Sensitizing dye>
It is preferable to add a sensitizing dye to the colored curable composition of the present invention as necessary. Exposure to a wavelength that can be absorbed by the sensitizing dye promotes radical generation reaction of the polymerization initiator component and polymerization reaction of the polymerizable compound thereby. Examples of such a sensitizing dye include a known spectral sensitizing dye or dye, or a dye or pigment that absorbs light and interacts with a photopolymerization initiator.

(Spectral sensitizing dye or dye)
Examples of the sensitizing dye used in the present invention include the compounds described in JP-A-2008-250295, paragraph numbers [0107] and [0109].

<Alkali-soluble resin>
In the colored curable composition of the present invention, an alkali-soluble resin can be used for the purpose of improving the film-forming property. Examples of the alkali-soluble resin that can be used in the present invention include the resins described in paragraph numbers [0111] to [0120] of JP-A-2008-266627.
The alkali-soluble resin is appropriately selected according to the purpose, and only one kind may be used or two or more kinds may be used in combination.
As content in the colored curable composition of alkali-soluble resin, 0-15 mass% is preferable in the total solid of this composition, More preferably, it is 1-12 mass%, Most preferably, it is 1 -10 mass%.

-Other components-
If necessary, the colored curable composition of the present invention includes a chain transfer agent, a thermal polymerization initiator, a thermal polymerization component, a thermal polymerization inhibitor, other fillers, a polymer compound other than the above alkali-soluble resin, and an interface. Various additives such as an activator, an adhesion promoter, an antioxidant, an ultraviolet absorber, and an aggregation inhibitor can be contained.

<Chain transfer agent>
Examples of the chain transfer agent which can be added to the colored curable composition of the present invention include N, N-dialkylaminobenzoic acid alkyl esters such as N, N-dimethylaminobenzoic acid ethyl ester, 2-mercaptobenzothiazole, 2 -Mercapto compounds having a heterocyclic ring such as mercaptobenzoxazole and 2-mercaptobenzimidazole, and aliphatic polyfunctional mercapto compounds.
A chain transfer agent may be used individually by 1 type, and may use 2 or more types together.

<Thermal polymerization initiator>
It is also effective to contain a thermal polymerization initiator in the colored curable composition of the present invention. Examples of the thermal polymerization initiator include various azo compounds and peroxide compounds. Examples of the azo compounds include azobis compounds. Examples of the peroxide compounds include ketones. Examples thereof include peroxides, peroxyketals, hydroperoxides, dialkyl peroxides, diacyl peroxides, peroxyesters, peroxydicarbonates, and the like.

<Thermal polymerization component>
It is also effective to contain a thermal polymerization component in the colored curable composition of the present invention. If necessary, an epoxy compound can be added to increase the strength of the coating film. Examples of the epoxy compound include the compounds described in paragraph No. [0154] of JP2008-275192A.
Specific preferred compounds for the thermal polymerization component include 3 ′, 5′-tetramethyl-4,4′diglycidylbiphenyl and the like. These are also available as commercial products, and preferable examples of the commercial products include Etototo YD-115, 118T, 127, YDF-170, YDPN-638, YDPN-701, Daicel Chemical, Plaxel. GL-61, GL-62, 3,5, Celoxide 2021, 2081, Epolide GT-302, GT-403, EHPE-3150, and the like.

<Surfactant>
The colored curable composition of the present invention is preferably composed of various surfactants from the viewpoint of improving coatability. Various surfactants such as fluorine-based, nonionic-based, cationic-based and anionic-based surfactants are used. Can be used. Of these, fluorine-based surfactants and nonionic surfactants are preferable.
Examples of the surfactant that can be used in the present invention include surfactants described in paragraph numbers [0156] to [0161] of JP-A-2008-275192.

  In addition to the above, various additives can be added to the colored curable composition. Specific examples of additives include ultraviolet absorbers such as 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole and alkoxybenzophenone, and anti-aggregation agents such as sodium polyacrylate. Fillers such as glass and alumina; itaconic acid copolymers, crotonic acid copolymers, maleic acid copolymers, partially esterified maleic acid copolymers, acidic cellulose derivatives, and acid anhydrides added to hydroxyl group-containing polymers And alcohol-soluble nylon, alkali-soluble resins such as phenoxy resin formed from bisphenol A and epichlorohydrin.

  Further, when the alkali solubility of the uncured part is promoted and the developability of the pigment dispersion composition is further improved, the pigment dispersion composition may be an organic carboxylic acid, preferably a low molecular weight organic carboxylic acid having a molecular weight of 1000 or less. Can be added. Specifically, for example, aliphatic monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, valeric acid, pivalic acid, caproic acid, diethyl acetic acid, enanthic acid, caprylic acid; oxalic acid, malonic acid, succinic acid, Aliphatic dicarboxylic acids such as glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, brassic acid, methylmalonic acid, ethylmalonic acid, dimethylmalonic acid, methylsuccinic acid, tetramethylsuccinic acid, citraconic acid; Aliphatic tricarboxylic acids such as tricarballylic acid, aconitic acid, camphoric acid; aromatic monocarboxylic acids such as benzoic acid, toluic acid, cumic acid, hemelitic acid, mesitylene acid; phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, Aromatic polycarboxylic acids such as trimesic acid, melophanoic acid, pyromellitic acid; phenylacetic acid Hydratropic acid, hydrocinnamic acid, mandelic acid, phenyl succinic acid, atropic acid, cinnamic acid, methyl cinnamate, benzyl cinnamate, cinnamylidene acetic acid, coumaric acid, other carboxylic acids such as umbellic acid.

<Thermal polymerization inhibitor>
In addition to the above, it is preferable to add a thermal polymerization inhibitor to the colored curable composition of the present invention. For example, hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, t-butylcatechol, benzoquinone, 4,4′-thiobis (3-methyl-6-tert-butylphenol), 2,2′-methylenebis (4-methyl-6-tert-butylphenol), 2-mercaptobenzimidazole, etc. Useful.

Since the colored curable composition of this invention contains the pigment dispersion composition of this invention, it is excellent in the dispersion stability of the pigment contained as a coloring agent. Moreover, the colored film produced using the colored curable composition of the present invention has high contrast and excellent surface smoothness because the color material is uniformly and stably dispersed.
Therefore, the colored curable composition of the present invention is preferably used for forming a colored region of a color filter.

<Color filter and manufacturing method thereof>
The color filter of the present invention is characterized by having a colored pattern formed on the substrate using the above-mentioned colored curable composition of the present invention. Hereinafter, the color filter of the present invention will be described in detail along with its manufacturing method.

In order to produce the color filter of the present invention, a colored curable composition film of the present invention is formed on a substrate by coating, and then pre-baking, exposure, and development are sequentially performed to form a colored pattern. do it.
By such a method, a color filter used for a liquid crystal display element or a solid-state imaging element can be manufactured with low process difficulty, high quality, and low cost.
Hereinafter, each step will be described in detail.

[Application]
In the present invention, in producing a color filter, a film of a colored curable composition is formed by coating. As a coating method, known methods such as spin, slit-and-spin, and slit can be used, but slit coating is preferably used from the viewpoint of productivity.
As a substrate used for the color filter of the present invention, for example, alkali-free glass, soda glass, Pyrex (registered trademark) glass, quartz glass used for liquid crystal display elements and the like, and those obtained by attaching a transparent conductive film to these, And a photoelectric conversion element substrate used for a solid-state imaging device or the like, for example, a silicone substrate or a plastic substrate.
On these substrates, a black matrix for isolating each pixel may be formed, or a transparent resin layer may be provided for promoting adhesion.
The plastic substrate preferably has a gas barrier layer and / or a solvent resistant layer on its surface.

In addition, a driving substrate (hereinafter referred to as “TFT type liquid crystal driving substrate”) on which a thin film transistor (TFT) of a thin film transistor (TFT) type color liquid crystal display device is disposed is used. In addition, a color filter formed using the colored curable composition of the present invention can be formed to produce a color filter.
Examples of the substrate in the TFT type liquid crystal driving substrate include glass, silicone, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide. These substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum deposition, etc., if desired. For example, a substrate in which a passivation film such as a silicon nitride film is formed on the surface of the TFT liquid crystal driving substrate can be used.

In the present invention, it is preferable to use slit coating as a method of applying the colored curable composition of the present invention to a substrate. The conditions for this slit coating differ depending on the size of the coated substrate. For example, when coating is applied to a fifth generation glass substrate (1100 mm × 1250 mm), the colored curable composition from the slit nozzle The discharge amount is usually 500 to 3000 microliters / second, preferably 800 to 2000 microliters / second, and the coating speed is usually 50 to 300 mm / second, preferably 100 to 250 mm / second. .
Moreover, as solid content of the colored curable composition used at this slit application | coating process, it is 10-23% normally, Preferably it is 13-20%.

When forming a coating film with the colored curable composition of the present invention on a substrate, the thickness of the coating film (after pre-baking treatment) is generally 0.3 to 5.0 μm, preferably 0.5 to 4 0.0 μm, most preferably 0.5 to 3.0 μm.
In the case of a color filter for a solid-state image sensor, the thickness of the coating film (after pre-baking treatment) is preferably in the range of 0.5 to 5.0 μm.

[Pre-bake]
As described above, it is preferable to perform pre-baking after the colored curable composition film of the present invention is formed on the substrate by a coating method.
If necessary, a vacuum treatment can be performed before pre-baking.
The vacuum drying conditions are such that the degree of vacuum is usually about 0.1 to 1.0 torr (13 to 133 Pa), preferably about 0.2 to 0.5 torr (27 to 67 Pa).
Moreover, when performing a prebaking process as needed, it is 50-140 degreeC using a hotplate, oven, etc., Preferably it is about 70-110 degreeC, and it carries out on the conditions for 10 to 300 seconds. it can. Note that high-frequency treatment or the like may be used in combination with the pre-bake treatment. The high frequency treatment can be used alone.

〔exposure〕
After the formed film is dried or pre-baked if desired, the coating film is exposed through a predetermined mask pattern. Also, scanning exposure can be applied according to the purpose.
The radiation used for exposure is particularly preferably ultraviolet rays such as g-line, h-line, i-line, and j-line.
When manufacturing a color filter for a liquid crystal display device, exposure using mainly h-line and i-line is preferably used by a proximity exposure machine and a mirror projection exposure machine.
Further, when manufacturing a color filter for a solid-state image sensor, it is preferable to mainly use i-line in a stepper exposure machine.
When manufacturing a color filter using a TFT type liquid crystal driving substrate, the photomask used is a pattern for forming a pixel (colored pattern) as well as a through hole or a U-shaped depression. The thing in which the pattern for forming is provided is used.

〔developing〕
Development is performed after the exposure. By this development, the uncured portion of the coating film after exposure is eluted into the developer, and only the cured portion remains on the substrate.
The development temperature is usually 20 to 30 ° C., and the development time is 20 to 90 seconds.
As the developer, the colored curable composition of the present invention is exposed and the exposed portion is polymerized and cured, and then the coating of the colored curable composition in the uncured portion is dissolved, while the cured portion is not dissolved. Any of them can be used.
Specifically, a developing solution obtained by combining various organic solvents or an alkaline aqueous solution can be used.

Examples of the organic solvent used in the developer include the solvents described above that can be used in preparing the colored curable composition of the present invention.
Examples of the alkaline aqueous solution include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, sodium oxalate, sodium metasuccinate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide. , Tetraethylammonium hydroxide, choline, pyrrole, piperidine, alkaline compounds such as 1,8-diazabicyclo- [5.4.0] -7-undecene, in a concentration of 0.001 to 10% by mass, preferably 0.01 An alkaline aqueous solution dissolved so as to be ˜1 mass% can be mentioned.
An appropriate amount of a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like can be added to the alkaline aqueous solution.

The development method may be any of a dip method, a shower method, a spray method, and the like, and may be combined with a swing method, a spin method, an ultrasonic method, or the like. Before the developer is touched, the surface to be developed can be previously moistened with water or the like to prevent uneven development. It is also possible to develop with the substrate tilted.
Further, when manufacturing a color filter for a solid-state image sensor, paddle development is also used.

After the development process, after a rinsing process for washing and removing excess developer, drying is performed, and then heat treatment (post-baking) is performed as necessary to complete the curing.
The rinse treatment is usually performed with pure water, but to save liquid, pure water is used in the final cleaning, and used pure water is used in the initial stage of cleaning. You may use the method of using a sound wave irradiation together.

After the rinse treatment, draining and drying are performed, and then a heat treatment at 100 ° C. to 250 ° C. is usually performed. This post-baking is heating after development for complete curing, and is preferably performed by heating at 200 ° C. to 250 ° C. (hard baking).
In this heat treatment (post-bake), the coating film after development is continuously or batch-treated using a heating means such as a hot plate, a convection oven (hot air circulation dryer) or a high-frequency heater so as to satisfy the above conditions. It can be done with a formula.
It is preferable to perform UV cleaning after post-baking and before applying the next color. The UV cleaning is capable of performing at the glass substrate cleaning machine or the like (e.g. LC4000, product of Hitachi Electronics Engineering Ltd. Co.), the UV irradiation dose is usually 100mJ ^/ cm ² ~1000mJ ^/ cm 2 approximately. By performing the UV cleaning, the development residue can be removed, and the pattern forming property of the next color can be improved.

The color filter of the present invention can be manufactured by sequentially performing the above steps.
In addition, a color filter in which a cured film (colored pattern) colored in a plurality of colors is formed by sequentially repeating the above process for each color (3 colors or 4 colors) according to the desired number of hues. can do.

<Solid-state imaging device>
The solid-state imaging device of the present invention includes a color filter having the light-shielding color filter of the present invention described above and pixels formed by a colored pattern film of another color (three colors or four colors) as necessary. Configured.
Since the solid-state imaging device of the present invention includes the light-shielding color filter of the present invention in which a decrease in light-shielding ability at the peripheral portion is suppressed, noise can be reduced and color reproducibility can be improved.
The configuration of the solid-state imaging device of the present invention is a configuration provided with the light-shielding color filter of the present invention, and is not particularly limited as long as it is a configuration that functions as a solid-state imaging device. The present invention has a light receiving element composed of a plurality of photodiodes and polysilicon forming a light receiving area of an image pickup element (CCD image sensor, CMOS image sensor, etc.), and the present invention is provided on the surface opposite to the light receiving element forming surface of the support. The structure etc. with which this light-shielding color filter was provided are mentioned.

  EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to the following examples unless it exceeds the gist thereof. Unless otherwise specified, “part” and “%” are based on mass.

Synthesis Example 1: Synthesis of grayed raft polymer 1]
In a 1000 ml three-necked flask, 14.0 g of benzyl methacrylate, 49 g of polymethyl methacrylate having a methacryloyl group at the end (AA-6: manufactured by Toagosei Co., Ltd.), 49 g of the following compound (i-1), 21 g of methacrylic acid, and V-601 ( (Wako Pure Chemical Industries, Ltd.) 1.1 g of 1-methyl-2-pyrrolidone solution (200 g) and 1-methyl-2-pyrrolidone (100 g) were added, heated to 90 ° C. in a nitrogen stream, and stirred for 2 hours. Further, 1.1 g of V-601 was added and stirred with heating, and then the temperature was raised to 90 ° C. and stirred for 2 hours. Thereafter, the reaction solution was cooled to room temperature and then poured into 7 L of water (liter; the same applies hereinafter) to precipitate a polymer compound. The precipitated polymer compound was collected by filtration, washed with water and dried to obtain 93 g of a polymer compound.
As a result of measuring the mass average molecular weight of the obtained polymer compound by gel permeation chromatography (GPC) using polystyrene as a standard substance, it was 15,000. The acid value of this polymer compound determined by titration was 83 mgKOH / g.

As described above, 1.0 g of p-methoxyphenol was added to 93 g of the polymer compound obtained in the 1000 ml three-necked flask, and further, 430 g of 1-methyl-2-pyrrolidone was added and dissolved, and ice containing ice water was added. Cooled in bath. After the temperature of the mixed solution reached 5 ° C. or lower, 71 g of 1,8-diazabicyclo [5.4.0] -7-undecene (DBU) was further added dropwise over 1 hour using a dropping funnel. After completion of dropping, the ice bath was removed and the mixture was further stirred for 8 hours.
The obtained reaction liquid was adjusted to pH 7 by adding concentrated hydrochloric acid, and then poured into 5 L of water to precipitate a polymer compound (polymer 1). Precipitated was collected by filtration polymer compound, washed with water and dried to obtain the purpose and to Heidelberg raft polymer 1 75 g. Thereafter, the grayed raft polymer 1 150 g was dissolved in methoxy propylene glycol 350 g, to obtain a 30 wt% solution.
The obtained polymer compound ^{1 H-NMR} of (grayed raft polymer 1) was measured, that 100% of the side chain group derived from the compound (i-1) is converted to an ethylene methacrylate groups was confirmed . The mass average molecular weight measured by gel permeation chromatography (GPC) using polystyrene as a standard substance was 14,000. Furthermore, when the acid value of this polymer compound was determined by titration, it was 97 mgKOH / g.
The resulting grayed rafts polymer 1 structure, by explicitly composition of the monomer as a raw material (the content), the weight average molecular weight, with an acid value, shown in Table 1 below. Incidentally, grayed RAFT polymer 1, In Table 1, simply referred to as "Polymer 1". The same applies to the following. In addition, the value calculated | required by polystyrene conversion by GPC method is employ | adopted here for the weight average molecular weight.

[Synthesis Example 2: Synthesis of specific graft polymer 2]
In a 1000 ml three-necked flask, 14.0 g of benzyl methacrylate, 5 mol of caprolactone 5 mol addition oligomer (Placcel FM5, manufactured by Daicel Chemical Industries), 49 g of compound (i-1), 21 g of methacrylic acid, and V-601 ( Wako Pure Chemical Industries, Ltd.) 1.1 g of 1-methyl-2-pyrrolidone solution 200 g and 1-methyl-2-pyrrolidone 100 g were added, heated to 90 ° C. in a nitrogen stream, and stirred for 2 hours. Further, 1.1 g of V-601 was added and stirred with heating, and then the temperature was raised to 90 ° C. and stirred for 2 hours. Thereafter, the reaction solution was cooled to room temperature and then poured into 7 L of water to precipitate a polymer compound. The precipitated polymer compound was collected by filtration, washed with water and dried to obtain 93 g of a polymer compound.
The obtained polymer compound was measured to have a mass average molecular weight of 21,000 by gel permeation chromatography (GPC) using polystyrene as a standard substance. The acid value of the polymer compound determined by titration was 84 mg KOH / g.

As described above, an ice bath in which 1.0 g of p-methoxyphenol was added to 93 g of the polymer compound obtained in the 1000 ml three-necked flask, 430 g of 1-methyl-2-pyrrolidone was further added and dissolved, and ice water was added. It was cooled with. After the temperature of the mixed solution reached 5 ° C. or lower, 71 g of 1,8-diazabicyclo [5.4.0] -7-undecene (DBU) was further added dropwise over 1 hour using a dropping funnel. After completion of dropping, the ice bath was removed and the mixture was further stirred for 8 hours. The obtained reaction solution was adjusted to pH 7 by adding concentrated hydrochloric acid and then poured into 5 L of water to precipitate a polymer compound (polymer 2). The precipitated polymer compound was collected by filtration, washed with water and dried to obtain 75 g of the intended specific graft polymer 2. Thereafter, 150 g of the specific graft polymer 2 was dissolved with 350 g of methoxypropylene glycol to obtain a 30 wt% solution.
When ¹ H-NMR of the obtained polymer compound (specific graft polymer 2) was measured, it was confirmed that 100% of the side chain groups derived from the compound (i-1) were converted to ethylene methacrylate groups. . The mass average molecular weight measured by gel permeation chromatography (GPC) using polystyrene as a standard substance was 19000. Furthermore, when the acid value of this polymer compound was determined by titration, it was 97 mgKOH / g.

(Synthesis of A-3)
Into a 500 mL three-necked flask, 160.0 g of ε-caprolactone and 18.3 g of 2-ethyl-1-hexanol were introduced and dissolved with stirring while blowing nitrogen. Monobutyltin oxide 0.1g was added and it heated at 100 degreeC. After 8 hours, it was cooled to 80 ° C. after confirming disappearance of the raw material by gas chromatography. After adding 0.1 g of 2,6-di-t-butyl-4-methylphenol, 22.2 g of 2-methacryloyloxyethyl isocyanate was added. After 5 hours, the disappearance of the raw material was confirmed by ¹ H-NMR, and then cooled to room temperature to obtain 200 g of a solid monomer (A-3). It was confirmed by ¹ H-NMR, IR, and mass spectrometry that the obtained compound was the exemplified monomer (A-3).

[Synthesis Example 3: Synthesis of specific graft polymer 3]
In a 1000 ml three-necked flask, 14.0 g of benzyl methacrylate, 49 g of A-3 synthesized above, 49 g of compound (i-1) (the above structure), 21 g of methacrylic acid, and 1.1 g of V-601 (manufactured by Wako Pure Chemical Industries, Ltd.) 200 g of 1-methyl-2-pyrrolidone solution and 100 g of 1-methyl-2-pyrrolidone were added, heated to 90 ° C. under a nitrogen stream, and stirred for 2 hours. Further, 1.1 g of V-601 was added and stirred with heating, and then the temperature was raised to 90 ° C. and stirred for 2 hours. Thereafter, the reaction solution was cooled to room temperature and then poured into 7 L of water to precipitate a polymer compound. The precipitated polymer compound was collected by filtration, washed with water and dried to obtain 93 g of a polymer compound.
It was 23,000 as a result of measuring the mass mean molecular weight of the obtained high molecular compound with the gel permeation chromatography method (GPC) which used polystyrene as the standard substance. The acid value of this polymer compound determined by titration was 83 mgKOH / g.

As described above, an ice bath in which 1.0 g of p-methoxyphenol was added to 93 g of the polymer compound obtained in the 1000 ml three-necked flask, 430 g of 1-methyl-2-pyrrolidone was further added and dissolved, and ice water was added. It was cooled with. After the temperature of the mixed solution reached 5 ° C. or lower, 71 g of 1,8-diazabicyclo [5.4.0] -7-undecene (DBU) was further added dropwise over 1 hour using a dropping funnel. After completion of dropping, the ice bath was removed and the mixture was further stirred for 8 hours. The obtained reaction liquid was adjusted to pH 7 by adding concentrated hydrochloric acid, and then poured into 5 L of water to precipitate a polymer compound (specific graft polymer 3). The precipitated polymer compound was collected by filtration, washed with water and dried to obtain 75 g of the intended specific graft polymer 3. After this. 350 g of the specific graft polymer 3 was dissolved in 817 g of methoxypropylene glycol to obtain a 30 wt% solution.
When ¹ H-NMR of the obtained polymer compound (specific graft polymer 3) was measured, it was confirmed that 100% of the side chain groups derived from the compound (i-1) were converted to ethylene methacrylate groups. . The mass average molecular weight measured by gel permeation chromatography (GPC) using polystyrene as a standard substance was 21,000. Furthermore, when the acid value of this polymer compound was determined by titration, it was 97 mgKOH / g.
Specific graft polymers 4-6 and specific graft polymers 8-10 were synthesized in the same manner as the specific graft polymers 1-3.

Na us, in Table 1, a monomer as a raw material for grayed raft polymer abbreviated notation as follows.
Benzyl methacrylate → (BzMA)
Illustrative monomer (M-1) → (M-1)
Illustrative monomer (M-11) → (M-11)
PLACCEL FM5 (trade name: manufactured by Daicel Chemical Industries, Ltd.) → (FM5)
Methacrylic acid → (MMA)
Acrylic acid → (AA)

Grayed raft polymer 1 6,8～ 10 obtained above are graft polymer obtained by pendant double bonds, both, AA-6 is at least macromer, PLACCEL FM5, and A-3 either It is a graft polymer comprising 5 to 30% by mass of at least one of acrylic acid and methacrylic acid in the main chain structure, which contains the above-mentioned structural unit as a copolymerization component.

( Reference Examples 1, 11, 13, Examples 2-6, 8-10, 12, 14)
<1. Preparation of pigment dispersion composition>
In the following composition (1), pigment, pigment derivative, the components of the grayed raft polymer, mixing the composition comprising as described in the following Table 2, stirred for 3 hours at a rotation speed 3,000rpm using a homogenizer And mixed to prepare a mixed solution containing the pigment.
[Composition (1)]
-Pigment (compound described in Table 2 below) 90 parts-Pigment derivative (compound described in Table 2 below) 10 parts-Polymer 30% propylene glycol monomethyl ether acetate solution 150 parts-1-methoxy-2-propyl acetate 600 copies

Subsequently, the obtained mixed solution was further subjected to a dispersion treatment for 6 hours with a bead disperser disperse mat (manufactured by GETZMANN) using 0.2 mmφ zirconia beads, and then further a high-pressure disperser NANO-3000 with a decompression mechanism. The dispersion treatment was performed at a flow rate of 500 g / min under a pressure of 2000 kg / cm 3 using -10 (manufactured by Miki Co.). This dispersion treatment was repeated 10 times to obtain pigment dispersion compositions (1) to (14) of Reference Examples and Examples .

(Performance evaluation of pigment dispersion)
<Evaluation of pigment dispersion composition>
The obtained pigment dispersion composition was evaluated in the following (1) and (2). The results are summarized in Table 2.

(1) Viscosity measurement and evaluation For the obtained pigment dispersion composition, using an E-type viscometer, the viscosity η1 of the pigment dispersion composition immediately after dispersion and the pigment dispersion composition after 1 week at room temperature after dispersion The viscosity η2 of the product was measured and the degree of thickening was evaluated. Here, the low viscosity indicates that the increase in viscosity due to the dispersant is suppressed, and the dispersibility and dispersion stability of the pigment are good.

(2) Measurement and Evaluation of Contrast The obtained pigment dispersion composition was applied on a glass substrate, and a sample was prepared so that the thickness of the coating film after drying was 1 μm. This sample was placed between two polarizing plates, the amount of transmitted light was measured when the polarization axis was parallel and when the polarization axis was parallel, and the ratio was taken as contrast. 512 color display 10.4 “size TFT-LCD color filter, planting, Koseki, Fukunaga, Yamanaka”). Here, a high contrast indicates that the pigment is uniformly dispersed in a highly refined state, and thus the transmittance, that is, the coloring power is high.

The details of the compounds used in Table 2 are shown below.
Polymer 1 Polymer 6, Polymer 8 - Polymer 10: grayed raft polymer 1 6,8～ 10 obtained in Synthesis Example.
Pigment R1: C.I. I. Pigment Red 254 Average primary particle size 30 nm
Pigment R2: C.I. I. Pigment Red 254 Average primary particle size 23 nm
Derivative A, Derivative B: Structure below

From Table 2, the pigment dispersion composition of the example using the specific graft polymer according to the present invention as a polymer dispersant has a small increase in viscosity over time and good dispersion stability. It can be seen that the colored film formed of the dispersion composition has a high contrast, whereby the pigment particles are finely dispersed.

[Examples 15 to 16, 18 to 19]
<Preparation of colored photocurable composition>
With pigment dispersion composition obtained as described above, to prepare a colored curable composition of the following.

Pigment dispersion composition (composition described in Table 3 below) 2000 parts Dipentaerythritol pentahexaacrylate (polymerizable compound) 100 parts 4- [o-bromo-pN, N-di (ethoxycarbonyl)
Aminophenyl] -2,6-di (trichloromethyl) -S-triazine (photopolymerization initiator) 30 parts benzyl methacrylate / methacrylic acid (= 75/25 [mass ratio]) copolymer (weight average molecular weight: 12,000) propylene glycol monomethyl ether acetate solution (solid content 30%) (alkali-soluble resin) 400 parts 1-methoxy-2-propyl acetate (solvent) 390 parts

<Preparation of color filter using colored curable composition>
The prepared colored curable composition (color resist solution) is heated on a hot plate on a 100 mm × 100 mm glass substrate (1737, manufactured by Corning) at a surface temperature of 120 ° C. for 120 seconds after coating. The spin coating speed was adjusted so that the film thickness of the film was 1.0 μm, and the film was uniformly coated on a silicon wafer to obtain a 1.0 μm coating film.
Then, i-line stepper, FPA-3000iS + through a photomask having a pattern of 3mm square using (Canon Co., Ltd.), the exposure amount of 100 mJ / cm ² or more 5000 mJ / cm ² or less in the range, 100 mJ Irradiation was performed while changing in steps of / cm ² . After the irradiation, paddle development is performed for 60 seconds at 23 ° C. using a 0.3% aqueous solution of tetramethylammonium hydroxide (TMAH), and then rinse is performed using pure water for 20 seconds in a spin shower. Washed with pure water. Thereafter, the adhered water droplets were removed with high-level air, and the substrate was naturally dried to obtain a colored pattern.
Then, the coating film that has been exposed and developed as described above is heat-treated in an oven at 220 ° C. for 1 hour (post-baking) to form a colored pattern (colored region) for the color filter on the glass substrate. A filter substrate (color filter) was produced.

<Evaluation of color filter>
The produced colored filter substrate (color filter) was evaluated as follows. The results are shown in Table 2 below.
(1) Contrast A polarizing plate is placed on the colored resin film of the colored filter substrate, and the colored resin film is sandwiched between them. The luminance when the polarizing plate is parallel and the luminance when the polarizing plate is orthogonal are obtained using BM-5 manufactured by Topcon Corporation. The value obtained by measuring and dividing the parallel brightness by the orthogonal brightness (= the parallel brightness / the orthogonal brightness) was used as an index for evaluating the contrast. Larger values indicate higher contrast.

(2) Solubility in alkali developer and evaluation of suspension in alkali developer 150 ml beaker with 100 g of 10% aqueous solution of alkali developer (trade name: CDK-1, manufactured by Fuji Film Electronics Materials Co., Ltd.) Measure.
On the other hand, the colored photosensitive composition was applied on a 100 mm × 100 mm glass substrate (trade name: manufactured by 1737 Corning) so as to have a film thickness of 2.5 μm and dried (prebaked) in an oven at 90 ° C. for 60 seconds. The glass was cut so that the sample had a size of 25 mm × 100 mm, and two of them were superposed so that the coated surface was on the outside, thereby preparing a measurement sample.
The measurement sample is dipped in the developer prepared as described above and the up-and-down operation of drawing it out is repeated 20 times, and the solubility of the coating film after pre-baking and the presence or absence of the suspension in the developer are visually observed. It was judged.
The immersion time in the developer was 1 second to 2 seconds per time.

The evaluation index is as follows. Here, the larger the index number, the better the developability of the coating film.
-Evaluation index-
5: The coating film is completely dissolved in the vertical movement 1 to 10 times, and there is no suspension in the alkaline developer 4: The coating film is completely dissolved in the vertical movement 11 to 20 times, and in the alkaline developer No suspension 3: The coating film is completely dissolved in 1 to 10 times in the vertical motion, but there is a suspension in the alkaline developer 2: The coating film is completely dissolved in 11 to 20 times in the vertical motion. There is a suspension in the developer 1: The coating film is insoluble even after 20 vertical movements

<Pattern cross-sectional shape>
The cross-sectional shape SEM of the formed pattern was observed.
The pattern cross-sectional shape is most preferably a forward taper, and a rectangular shape is next preferred. Reverse taper is not preferred.

<Board adhesion>
The evaluation of the substrate adhesion was performed by observing whether or not a pattern defect occurred. The evaluation criteria are as follows.
-Evaluation criteria-
○: No pattern defect was observed.
(Triangle | delta): Although the pattern defect | defect was hardly observed, the defect | deletion was partially observed.
X: A pattern defect was remarkably observed.

Incidentally, the pigment dispersion composition in Table 3 (3), (4), (8) and (12), Example 3, Example 4, the actual施例8, and the pigment dispersion obtained in Example 12 It is a composition.
From the results in Table 3, the colored pattern formed by the colored curable composition prepared using the pigment dispersion composition of the present invention has few development residues, the pattern shape is good, and the substrate adhesion is excellent. The color filter having such a coloring pattern had high contrast.

[ Reference Example 20, Examples 2 1 to 25, 27 to 29]
<Preparation of pigment dispersion composition>
A pigment mixed solution was prepared in the same manner as in Reference Example 1 according to the following composition (2).
[Composition (2)]
・ C. I. Pigment Green 36 (average primary particle size: 20 nm) 55 parts C.I. I. Pigment Yellow 150 (average primary particle size: 24 nm) 45 parts 30% propylene glycol monomethyl ether acetate solution of the specific graft polymer shown in Table 4 180 parts 1-methoxy-2-propyl acetate 750 parts

Subsequently, the mixed solution obtained above was further subjected to a dispersion treatment for 6 hours using a bead disperser disperse mat (manufactured by GETZMANN) using 0.3 mmφ zirconia beads, and then further a high-pressure disperser NANO with a decompression mechanism. The dispersion treatment was performed at a flow rate of 500 g / min under a pressure of 2000 kg / cm ³ using −3000-10 (manufactured by Miki Co., Ltd.). This dispersion treatment was repeated 10 times to obtain pigment dispersion compositions of Reference Examples and Examples .

The obtained pigment dispersion composition was evaluated in the same manner as in Reference Example 1, and the results are also shown in Table 4 above.
From the results of Table 4, the pigment dispersion compositions of Examples using the specific graft polymer according to the present invention as a polymer dispersant have a small increase in viscosity after aging and good dispersion stability. It can be seen that the colored film formed by the pigment dispersion composition has high contrast, whereby the pigment particles are finely dispersed.

[Examples 30 to 32, 34]
<Preparation of colored curable composition>
With pigment dispersion composition obtained as described above, to prepare a colored curable composition of the following.

Pigment dispersion composition (composition described in Table 5 below) 2000 parts Dipentaerythritol pentahexaacrylate (polymerizable compound) 100 parts 4- [o-bromo-pN, N-di (ethoxycarbonyl)
Aminophenyl] -2,6-di (trichloromethyl) -S-triazine (photopolymerization initiator) 30 parts benzyl methacrylate / methacrylic acid (= 75/25 [mass ratio]) copolymer (weight average molecular weight: 12,000) propylene glycol monomethyl ether acetate solution (solid content 30%) (alkali-soluble resin) 400 parts 1-methoxy-2-propyl acetate (solvent) 390 parts

<Preparation of color filter using colored curable composition>
The obtained colored curable composition (color resist solution) was applied on a 100 mm × 100 mm glass substrate (1737, manufactured by Corning) so that the x value serving as an index of color density was 0.650. Thereafter, in the same manner as in Examples 15 to 19, a colored pattern (colored region) for a color filter was formed on a glass substrate to produce a colored filter substrate (color filter).

<Evaluation of colored curable composition and color filter>
About the produced colored curable composition and colored filter substrate (color filter), as in Examples 15 to 19, (1) contrast, and (2) solubility in alkaline developer, and in alkaline developer The suspension was evaluated. The substrate adhesion and pattern shape were also evaluated in the same manner. Furthermore, the following evaluation was performed for color unevenness.
<Evaluation of uneven color>
In the same manner as the coating film described above, a glass substrate with an undercoat layer is prepared by applying a resist solution on a glass plate, a colored curable composition is applied on the glass with an undercoat layer, and a colored layer (coated) Film). Heat treatment (pre-baking) was performed for 120 seconds using a hot plate at 100 ° C. so that the dry film thickness of the coating film became 0.7 μm. The luminance distribution of the coated glass plate was analyzed from an image taken with a microscope MX-50 (Olympus).
The luminance distribution was analyzed, and the color unevenness was evaluated based on the ratio of the pixels whose deviation from the average is within ± 5% to the total number of pixels. The evaluation criteria are as follows.

-Evaluation criteria-
○: Pixels whose deviation from the average is within ± 5% is 99% or more of the total number of pixels. Δ: Pixels whose deviation from the average is within ± 5% is 95% or more and less than 99% of the total number of pixels. : Pixels whose deviation from the average is within ± 5% is less than 95% of the total number of pixels. The evaluation results are summarized in Table 5 below.

Incidentally, the pigment dispersion composition in Table 5 (17), (18), (20)及 Beauty (24), pigment obtained in Example 22, Example 23, Example 2 5及 beauty Example 29 It is a dispersion composition.
From the results in Table 5, the colored pattern formed by the colored curable composition prepared using the pigment dispersion composition of the present invention has few development residues, the pattern shape is good, and the substrate adhesion is excellent. It can be seen that the color filter having such a coloring pattern has characteristics of high contrast and little color unevenness.

Example 35
<Production of solid-state image sensor>
-Preparation of colored curable composition-
In the same manner as in Example 15 except that the polymer 2 prepared in Synthesis Example 2 was used and the following chromatic pigment was used as a colorant, red (R) colored polymerizable composition R-1, green ( G) colored polymerizable composition G-1 and blue (B) colored polymerizable composition B-1 were prepared.

Chromatic pigment for forming curable composition for each color of RGB, pigment for red (R) C.I. I. Pigment Red 254
-Green (G) pigment C.I. I. Pigment Green 36 and C.I. I. Pigment Yellow 219 30/70 [mass ratio] mixture and blue (B) pigment C.I. I. Pigment Blue 15: 6 and C.I. I. 30/70 [mass ratio] mixture with Pigment Violet 23 -Preparation of color filter for solid-state image sensor-
A 1.5 × 1.5 μm red (R) colored pattern was formed in the same manner as in Example 15 using the prepared colored polymerizable composition. Further, in the same manner, 1.5 × 1.5 μm green (G) and blue (B) colored polymerizable composition B-1 were used using green (G) colored polymerizable composition G-1. A blue (B) chromatic coloring pattern was sequentially formed to produce a color filter for a solid-state imaging device. When the pattern shape formed in the same manner as in Example 15 was observed, it was confirmed that a forward tapered pattern was formed.
From the results of Example 35, the colored curable composition of the present invention is a color filter for use in a liquid crystal display device even when a color filter for use in a solid-state imaging device having a fine coloring pattern of 1.5 μm square is produced. It can be seen that excellent pattern formability is achieved as in the case of manufacturing.
Further, when this color filter was incorporated into an individual image sensor, it was confirmed that the resolution showed no problem in practical use.

Claims (10)

(A) An unsaturated double bond is pendant on a side chain of a polymer containing 5% by mass to 30% by mass of a copolymer component of at least one of acrylic acid and methacrylic acid in the main chain skeleton, and the following general formula (1) Graft type polymer having at least one repeating unit selected from repeating units represented by formula (2), (B) pigment, and (C) pigment dispersion containing organic solvent Composition.

[In General Formulas (1) and (2), R ¹ , R ² , R ⁴ , and R ⁵ each represent a hydrogen atom, and R ³ and R ⁶ each independently represent a hydrogen atom or a methyl group . X ¹ and ^{X 2} are each independently, - C (= O) O - represents a. L ¹ and L ² each independently represent an ethylene group or —C ₂ H ₄ —NHC (═O) — . A ¹ and A ² each independently represents a linear substituted or unsubstituted alkyl group having 4 to 15 carbon atoms or a branched substituted or unsubstituted alkyl group having 4 to 15 carbon atoms. Represent. m and n represent 5 . p and q are each independently an integer of 4-10. ]   (A) An unsaturated double bond is pendant on the side chain of the polymer containing at least one of acrylic acid and methacrylic acid as a copolymer component in the main chain skeleton, The graft polymer having at least one repeating unit selected from the repeating units represented by the formula (1) and the general formula (2) further contains a heterocyclic structure in the side chain, and has a weight. The pigment dispersion composition according to claim 1, which has an average molecular weight of 1,000 to 100,000.   The pigment dispersion according to claim 1 or 2, wherein the ratio (mass ratio) of acrylic acid is 80 or more when the total amount of acrylic acid and methacrylic acid contained as a copolymerization component in the graft polymer is 100. Composition.   The average primary particle diameter of said (B) pigment is the range of 10 nm-25 nm, The pigment dispersion composition of any one of Claims 1-3.   The pigment dispersion composition according to any one of claims 1 to 4, which is used for forming a colored region in a color filter.   The colored curable composition containing the pigment dispersion composition of any one of Claims 1-5, (D) polymeric compound, and (E) photoinitiator.   The colored curable composition according to claim 6, wherein the pigment concentration is 35% by mass or more and 90% by mass or less.   A color filter comprising a colored pattern formed using the colored curable composition according to claim 6 on a substrate.   A liquid crystal display device comprising the color filter according to claim 8. A solid-state imaging device comprising the color filter according to claim 8 .